JP2010517096A - Optical element comprising a compatible coating and method for making an optical element comprising a compatible coating - Google Patents

Abstract

The present invention relates to an optical element such as an ophthalmic element, the optical element comprising a substrate, a compatible coating optionally comprising a dendritic polymer on at least a portion of the surface of the substrate, and the substrate Including a functional organic coating in contact with at least a portion of the compatible coating at a position opposite the material, including, but not limited to, an alignment coating, a photochromic coating, or an alignment liquid crystal coating . The present invention also provides a dendritic polymer compatible coating composition that can be used to form a compatible coating on the surface of the optical element, and a method for making an optical element using the compatible coating. About.

Description

(background)
The present invention relates generally to optical elements (eg, ophthalmic elements), which include a substrate, a compatible coating, and a functional organic coating on at least a portion of the surface of the substrate. The present invention also relates to a compatible coating composition that can be used to form a compatible coating on the surface of the optical element, and a method for making an optical element comprising the compatible coating.

  An optical element (eg, an ophthalmic element) can be adapted for use in a particular application by applying one or more functional organic coatings to the element. For example, optical elements (eg, ophthalmic elements) can be adapted for use in photochromic eyewear applications by applying a photochromic coating to the surface of the element. An ophthalmic element having a photochromic coating (eg, a photochromic lens for eyewear applications) can provide the wearer with an appropriate level of transmitted light, depending on ambient conditions.

  Further, an optical element (eg, an ophthalmic element) for use in polarizing applications is adapted by forming a polarizing coating comprising an aligned liquid crystal material and a dichroic dye on the surface of the element. Is possible. Ophthalmic elements having a polarizing coating (eg, polarizing lenses for eyewear applications) provide the wearer with reduced reflected light by linearly polarizing a percentage of the light transmitted through the element To do.

  Adapting the optical element to exhibit both photochromic and dichroic characteristics under certain conditions by forming a coating comprising an aligned liquid crystal material and a photochromic-dichroic dye on the surface of the element Is also possible. An optical element having a photochromic-dichroic coating can switch from a first state (eg, a transparent unpolarized state) to a second state (eg, a colored polarization state) in response to actinic radiation, and In the absence of actinic radiation and in response to thermal energy, the first state can be restored. For example, an ophthalmic element having a photochromic-dichroic coating (eg, a lens for eyewear applications) transitions between a transparent unpolarized state and a colored polarization state, depending on ambient conditions. Thus, the wearer may be provided with both an appropriate level of transmitted light and reduced reflected light.

  However, if the interaction between the functional organic coating and the surface to which the functional organic coating is applied is insufficient, the functional organic coating (or a part thereof) is applied to the surface. May not adhere properly. For example, if the liquid crystal coating (eg, those discussed above) and the substrate surface lack sufficient suitability, the coating may not adhere properly to the surface, and the surface From, for example, it can be easily removed by peeling. Allowing unpolarized light to pass through the portion of the lens from which the coating has been removed when the polarizing coating peels off the surface of the lens in the context of a lens for ophthalmic applications. Reduces the overall performance of the lens.

  It is possible to apply a compatible coating to the surface of the substrate to improve the compatibility between the substrate and the photochromic coating applied to the substrate. However, the compatible coating used with one coating / surface combination may not provide adequate compatibility between the same surface and a different coating. Thus, different coating / surface combinations may require the use of different compatible coatings.

  However, the need to use different compatible coatings with different coating / surface combinations can lead to, inter alia, manufacturing inefficiencies and increased costs. Thus, it would be advantageous to develop compatible coatings that can be used to enhance the compatibility of various coating / surface combinations to provide a satisfactory compatibility between the coating and the surface.

  Various non-limiting embodiments of the present disclosure provide optical elements and methods for forming the optical elements. For example, the present disclosure provides an optical element, the optical element being a substrate, a compatible coating comprising a dendritic polymer on at least a portion of the surface of the substrate; and the opposite of the substrate A functional organic coating other than an abrasion resistant coating in contact with at least a portion of the compatible coating.

  The present disclosure also provides a method for making an optical element. The method includes forming a compatible coating comprising a dendritic polymer on at least a portion of a surface of a substrate, and functionality other than an abrasion resistant coating on at least a portion of the compatible coating. Forming an organic coating, such that the functional organic coating is in contact with at least a portion of the compatible coating at a location opposite the surface of the substrate.

  Furthermore, the present disclosure provides compatible coating compositions. The compatible coating composition is a dendritic polymer containing terminal functional groups, an epoxy-containing material containing at least two reactive functional groups, and at least one of the at least two reactive functional groups is: An epoxy-containing material that is an epoxy group, an aminoplast resin containing at least two reactive groups, a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof, and an initiator, wherein the compatible coating composition The object is essentially free of photochromic material.

  The present invention also relates to an optical element, wherein the optical element is a substrate, a compatible coating on at least a portion of the surface of the substrate, and a functionality on at least a portion of the compatible coating. Includes organic coating. The compatible coating is obtained from a compatible coating composition as described herein.

  A method for forming an ophthalmic element is also provided, the method comprising forming a compatible coating on at least a portion of the surface of the substrate, and on at least a portion of the compatible coating. Forming a functional organic coating. The compatible coating is obtained from a compatible coating composition as described herein.

  The present disclosure provides an ophthalmic element, wherein the ophthalmic element is an ophthalmic substrate, a compatible coating essentially free of photochromic material on at least a portion of the surface of the ophthalmic substrate, And a functional organic coating other than an abrasion resistant coating in contact with at least a portion of the compatible coating at a position opposite the ophthalmic substrate. The compatible coating is formed from a compatible coating composition, the compatible coating composition comprising an isocyanate-containing material comprising at least two isocyanate groups; a (meth) acrylate-containing material comprising at least two reactive functional groups. Wherein at least one of the at least two reactive functional groups is a (meth) acrylate group; a (meth) acrylate-containing material; an aminoplast resin containing at least two reactive groups; coupling An agent, at least a partial hydrolyzate thereof, or a mixture thereof; and at least one of an initiator and a catalyst.

  A method for forming an ophthalmic element is also disclosed. The method includes the steps of forming a compatible coating essentially free of photochromic material on at least a portion of the surface of the ophthalmic substrate, wherein at least a portion of the compatible coating is irradiated with UV radiation, electron beam radiation. And at least partially curing at least a portion of the compatible coating by exposure to at least one of thermal radiation, and a function other than a hard coating on at least a portion of the compatible coating Forming a conductive organic coating. The compatible coating is obtained from a compatible coating composition as described herein.

(Brief explanation of several ways of viewing the drawings)
Aspects of the invention are better understood when read in conjunction with the drawings.
FIG. 1 is a schematic cross-sectional view of an optical element according to the present invention. FIG. 2 is a schematic cross-sectional view of an optical element according to the present invention. FIG. 3 is a schematic cross-sectional view of an optical element according to the present invention.

(Description of various non-limiting embodiments)
The present invention is described herein, along with specific embodiments and examples, but instead encompasses modifications within the spirit and scope of the invention as defined by the appended claims. It is to be understood that the invention is not limited to the specific embodiments and examples disclosed above except. Further, it is to be understood that this description illustrates aspects of the invention in connection with a clear understanding of the invention. Accordingly, certain aspects of the invention that will be apparent to those skilled in the art and therefore do not facilitate a better understanding of the invention are not shown in order to simplify the description.

  As used herein and in the appended claims, the articles "one, a", "one," and "the, the" are clearly And expressly and unequally, including multiple indications unless limited to one indication. Further, for purposes of this specification, unless otherwise indicated, all numbers representing the amounts used herein (eg, weight percentages and processing parameters), as well as other properties or parameters, are in all cases Should be understood to be modified by the term “about”. Thus, unless otherwise indicated, it should be understood that the numerical parameters set forth in the following specification and attached claims are approximations. At least, and not as an intention to limit the application of the doctrine of equivalents to the claims, the numerical parameters are in view of the number of reported significant digits and the application of ordinary rounding techniques. Should be read.

  Further, the numerical ranges and parameters indicating the broad scope of the present invention are approximate as discussed above, but the numerical values shown in the Examples section are reported as accurately as possible. However, it is to be understood that such numerical values inherently include certain errors arising from, for example, measurement devices and / or measurement techniques. Further, where numerical ranges are described herein, these ranges include the indicated ranges and indicated points.

  In addition, a list of possible substituents can be found, for example, in headings or subheadings such as (a), (b) ...; (1), (2) ...; (i), (ii) ...; It should be recognized that these headings or subheadings are provided only for readability and are not intended to limit the choice of substituents, as provided herein using subheading). is there.

  As discussed above, the present invention relates to an optical element, and in particular, to a substrate, a compatible coating on at least a portion of the surface of the substrate, and a position opposite the substrate. It relates to an optical element comprising a functional organic coating other than an abrasion resistant coating in contact with at least a portion of the compatible coating. That is, the compatible coating is present between the substrate and the functional organic coating.

  As used herein, the term “optical, optical” means related to or associated with light and / or vision. Non-limiting examples of optical elements include ophthalmic elements, display elements, windows, mirrors, and active and passive liquid crystal cells. As used herein, the term “ophthalmic, ophthalmic” means related to or associated with the eye and vision. Non-limiting examples of ophthalmic elements include segmented multi-vision lenses or non-segmented compound lenses (eg, bifocal lenses, trifocal lenses, and progressive lenses). Corrective and non-corrective lenses, including but not limited to single-lens or multi-vision lenses, and vision (aesthetically or otherwise) Other elements used to correct, protect, or enhance include, but are not limited to, contact lenses, intraocular lenses, magnifying lenses, and protective lenses or visors.

  As used herein, the term “display” means a visible or machine-readable display of information in words, numbers, symbols, designs and figures. Non-limiting examples of display elements include screens, monitors, and security elements (eg, security marks). As used herein, the term “window” means an aperture that is adapted to allow transmission of light therethrough. Non-limiting examples of windows include automotive and aircraft transparencies, filters, shutters, and optical switches. As used herein, the term “mirror” means a surface that reflects most of the incident light like a mirror. As used herein, the term “liquid crystal cell” refers to a structure that includes a liquid crystal material capable of alignment. In a typical liquid crystal cell, the liquid crystal material is contained between two substrates that are sealed together to form a chamber. An active liquid crystal cell is a cell in which the liquid crystal material can be switched between a conditioned state and a disordered state, or between two conditioned states by the application of an external force (eg, an electric or magnetic field). is there. A passive liquid crystal cell is a cell that maintains the state in which the liquid crystal material is arranged. One non-limiting example of an active liquid crystal cell element is a liquid crystal display.

  Substrates suitable for use with the various non-limiting embodiments of the invention disclosed herein include substrates formed from organic materials, inorganic materials, or combinations thereof (eg, composites). However, it is not limited to these. Further, the substrate disclosed herein may have any suitable shape, including planar, cylindrical, spherical, plano-concave (ie, one side is flat and the other is Side surfaces are concave) and plano-convex (ie, one side is flat and the other side is convex), but is not limited thereto. For example, the substrate may be a plano-convex or plano-concave ophthalmic lens, one having a flat surface and the other a curved (convex or concave) surface, the curved surface being ophthalmic It has a curvature corresponding to any of the various basic curves used for the lens. Specific non-limiting examples of materials from which the substrate is formed are described in more detail below.

  Non-limiting examples of organic materials that can be used to form the substrate disclosed herein include US Pat. No. 5,962,617, column 2, line 9 to column 7. Line 46 and US Pat. No. 5,658,501, column 15, line 28 to column 16, line 17 (the disclosures of which are specifically incorporated herein by reference). Included are polymeric materials (eg, homopolymers and copolymers) prepared from the disclosed monomers and monomer mixtures. Such an organic substance may be a thermoplastic polymer material or a thermosetting polymer material, and may be transparent or optically clear. And can have any required refractive index. For example, but not limiting herein, the refractive index of transparent or optically clear organic polymer materials from which ophthalmic lenses can be formed typically ranges from 1.48 to 1.74.

Specific non-limiting examples of monomers and polymers that can be used to form the substrate of the optical elements disclosed herein can include the following: polyol (allyl carbonate) monomers (eg, diethylene glycol) Bis (allyl carbonate) (this monomer is allyl diglycol carbonate such as sold by PPG Industries, Inc., Pittsburgh, Pennsylvania under the trademark CR-39 ^™ ); for example, polyurethane prepolymer and diamine cure Polyurea-polyurethane (polyurea-urethane) polymer, PPG Industries Ohio, Inc., prepared by reaction with an agent. A composition for certain such polymers sold under the trademark TRIVEX ^™ by C., Cleveland, Ohio; acrylic functional monomers (eg, carbonate monomers terminated with polyol (meth) acryloyl, diethylene glycol di) Methacrylate monomers, ethoxylated phenol methacrylate monomers, ethoxylated trimethylolpropane triacrylate monomers, ethylene glycol bismethacrylate monomers, poly (ethylene glycol) bismethacrylate monomers, urethane acrylate monomers, and poly (ethoxylated bisphenol A dimethacrylate) monomers; Isopropenylbenzene monomer; poly (vinyl acetate); poly (vinyl alcohol) Poly) (polyvinyl chloride); poly (vinylidene chloride); polyethylene; polypropylene; polyurethane; polythiourethane (for example, the specified optical resins MR-6, MR-7, and MR-- of Mitsui Totsu Chemicals, Inc.) Materials such as, but not limited to, thermoplastic polycarbonates (eg, carbonate linking resins obtained from bisphenol A and phosgene (one such material under the trademark LEXAN® ⁾ (Commercially available)); polyesters (for example materials marketed under the ^trademark MYLAR®); poly (ethylene terephthalate); polyvinyl butyral; norbornene homopolymers and copolymers (for example JSR Corp, Saitama, materials sold under the Japanese trademark ARTON ^{(registered trademark)),} poly (methyl methacrylate) (e.g., trademark PLEXIGLAS ^{(registered trademark)} materials are available commercially under) and and polyfunctional isocyanates By reacting with polythiol or polyepisulfide monomers (polythiols, polyisocyanates, polyisothiocyanates, and optionally homopolymerized or copolymerized with ethylene unsaturated monomers or halogenated aromatic-containing vinyl monomers) Or polymers that are either terpolymerized) include, but are not limited to, polymers prepared. For example, copolymers of such monomers and blends of the above polymers and copolymers with other polymers are also contemplated to form block copolymers or osmotic network products.

  As mentioned above, the substrate can be an ophthalmic substrate. As used herein, the term “ophthalmic substrate” refers to lenses, partially formed lenses, and lens blanks. Non-limiting examples of organic materials from which ophthalmic substrates can be formed according to various non-limiting embodiments disclosed herein include forming transparent or optically transparent castings for optical applications. Examples include, but are not limited to, art-recognized polymers that are useful in this regard.

  Other non-limiting examples of organic materials suitable for use in forming the substrates disclosed herein can include both synthetic and natural organic materials, these synthetic organic materials And natural organic materials include, but are not limited to, opaque or translucent polymeric materials, natural and synthetic textiles, and cellulosic materials. Non-limiting examples of inorganic materials suitable for use in forming substrates that can be used with the various non-limiting embodiments disclosed herein include inorganic oxide-based glasses, minerals, ceramics, and A metal is mentioned. For example, the substrate can include an inorganic oxide based glass. The base material may include a ceramic, metal, or mineral base material, and if necessary, at least one side surface may be polished to form a reflective surface. Where it is desirable to have a reflective substrate surface, a reflective coating or layer can be deposited or otherwise applied to the surface of an inorganic or organic substrate to make it reflective or its reflective Can increase sex.

  Furthermore, the substrate may be uncolored, colored and / or photochromic. As used herein, the term “uncolored substrate” means a substrate that is essentially free of colorant additions (eg, including but not limited to conventional dyes). To do. As used herein, the term “chemical radiation” refers to electromagnetic radiation, including but not limited to ultraviolet light and visible radiation that can cause a response. In addition, the term “colored substrate” means a substrate having colorant additions (eg, including but not limited to conventional dyes), where the colorant is actinic radiation. In response, it has a visible absorption spectrum that does not change significantly. As used herein, the term “photochromic substrate” means a substrate having a photochromic material addition. Further, the substrate according to various non-limiting embodiments disclosed herein can be colored and photochromic. That is, the substrate can include both conventional dyes, colorants (having a visible absorption spectrum that does not change significantly in response to actinic radiation) and photochromic materials.

Still further, the substrate of the optical element has a protective coating (eg, including but not limited to an abrasion resistant coating (also referred to as a “hard coat”) on one or more of its surfaces. Can do. For example, commercially available thermoplastic polycarbonate ophthalmic lens substrates are often sold with an abrasion resistant coating applied to their surfaces. This is because the surfaces of these substrates are easily scratched, easily worn or scratched. An example of one such polycarbonate lens substrate is sold under the trademark GENTEX® ⁽ by Gentex Optics, Inc., Dudley, Massachusetts).

As used herein, the term “protective coating” refers to coatings such as transition coatings, abrasion resistant coatings (or hard coats), oxygen barrier coatings, and UV shielding coatings. Non-limiting examples of wear-resistant coatings include wear-resistant coatings that include silane, wear-resistant coatings that include light-cured acrylate-based thin films, inorganic materials (eg, silica, titanium dioxide and / or zirconium dioxide) Abrasion resistant coatings based on these, as well as combinations of these coatings. For example, the protective coating can include a first coating of a light cured acrylate-based thin film and a second coating comprising silane. Non-limiting examples of commercially available protective coating products, Silvue ^(R) 124 and HI-GARD ^(R) coatings (respectively, SDC Coatings, Inc. And PPG Industries, commercially available from Inc.) Include It is done.

  Although not limited herein, some functional organic coatings (eg, alignment coatings that include a photoalignment material (eg, polyvinyl cinnamate) and coatings that include a liquid crystal material (ie, a liquid crystal coating) can be applied to an organic substrate surface. It has been observed by the inventors that, in particular, the conformable coating of the present invention can have a functional coating ( It has also been observed that it can be useful, for example, in improving and / or enhancing the adhesion of ophthalmic substrates, in particular alignment coatings and liquid crystal coatings to ophthalmic substrates having hard-coated surfaces. Therefore, the optical element of the present invention is in contact with at least a part of the surface of the substrate. A substrate comprising a wear resistant coating that is on the substrate in contact with at least a portion of the wear resistant coating on the surface of the substrate. Adhesion between the wear resistant coating and the functional organic coating applied thereon may be improved or enhanced.

  As discussed above, the present invention relates to a substrate, a compatible coating on at least a portion of the surface of the substrate, and at least one of the compatible coating at a position opposite the substrate. It relates to an optical element comprising a functional organic coating other than an abrasion resistant coating in contact with the part. As used herein, the term “coating” refers to a structure comprising one or more complete or partial layers derived from a flowable composition (this is a uniform composition and / or cross-sectional pressure). May or may not be). As used herein, the term “compatible coating” improves the compatibility between a surface and another coating applied thereon, and / or other coatings on the surface. Refers to a coating that facilitates the formation or application of. For example, a conformal coating may be used to improve the wettability, chemical compatibility, and adhesion of another coating to a surface (eg, the surface of a substrate or the surface of another coating). ).

  Further, as used herein in the context of “on” a surface or object, the term “on” means that the coating of the invention is supported or retained by the surface or object. As such, it means that the coating of the present invention is connected to the surface or object. Further, as used herein, the term “connected to” means bound directly or indirectly through another substance or structure. Thus, for example, a coating “on” a surface may be applied directly on the surface, or one or more other coatings, at least one of which is applied directly on the surface May be applied on top of.

  The compatible coating on at least a portion of the surface of the substrate includes a dendritic polymer. As used herein, the term “dendritic polymer” refers to a three-dimensional polymeric material comprising a multivalent core that is covalently bonded to a plurality of dendritic structures (or tree-like structures). The term “dendron” refers to a tree-like structure having multiple branch layers (or “generations”) emanating from a single focal point (eg, a multivalent core). means. Each successive branch layer or generation of the dendritic structure extends from a previous generation, and each branch layer or generation in the dendritic structure has one or more terminal reactive sites (or “terminal functional groups”). Can have successive generations (if any) extending from the terminal reactive sites, or in the last generation, the terminal reactive sites provide terminal functional groups to the dendritic polymer Can do. Dendritic polymers generally have a very large number of terminal functional groups, are entangled and have a low hydrodynamic volume. Further, as used herein, the term “dendritic polymer” includes both “dendrimers” and “dendritic branched polymers”. As used herein, the term “dendrimer” refers to a dendritic polymer having a symmetrical spherical shape that results from a controlled process that essentially provides a monodisperse molecular weight distribution. As used herein, the term “dendritic branched polymer” refers to a dendritic polymer that has some degree of asymmetry and a polydisperse molecular weight distribution.

  Although not limited herein, the dendritic polymer can be formed, for example, by stepwise forming a dendritic structure on a multivalent core. For example, but not limited herein, a polyester-type dendritic polymer includes a polyol core and a first chain extender (for example, but not limited to, a carboxylic acid containing two or more hydroxyl groups). Can be reacted under typical esterification conditions to form a core having several dendritic structures comprising a first branch layer (or generation) attached to the core. Each of the dendritic structures includes a number of terminal functional groups (for example, terminal hydroxyl groups in this example), and the terminal functional groups are located on the periphery of the first branch layer. These terminal functional groups can be further reacted with another first chain extender to produce a second branched layer on the core. Successive branch layer repeats by reacting the terminal functional groups at the periphery of the branch layer formed immediately before with a further first chain extender create the dendritic structure, Usually this results in an increase in the number of terminal functional groups (eg, terminal hydroxyl groups in this example) on the dendritic polymer. After the final branch layer is added to the dendritic polymer, any remaining terminal functional groups in the final branch layer of the dendritic polymer (eg, any remaining terminal hydroxyl groups in this example). Groups) can form terminal functional groups of the dendritic polymer; can be further chain extended, for example by alkoxylation; can be terminated, for example, by reaction with a chain terminator; or can react with another substance Can be functionalized by providing different terminal functional groups on the dendritic polymer. As used herein, the term “chain terminator” includes chain extenders that lack a suitable functional group to react with subsequent chain extenders.

  One non-limiting example of a step-wise method for forming a polyester-type dendritic polymer on a multivalent core is described in US Pat. No. 5,418,301 (“the '301 patent”), column 6, column 1 It is described in the lines from the 60th line. The '301 patent also provides some examples of multivalent cores suitable for use in forming polyester-type dendritic polymers in column 2, line 45 to column 3, line 68; In lines 5-55, some examples of chain extenders suitable for use in forming a polyester-type dendritic polymer, and in column 4, lines 56-5, line 68, polyester type Some examples of chain terminators suitable for use in the formation of dendritic polymers are provided. The foregoing portion of the disclosure of the '301 patent is specifically incorporated by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein.

  Furthermore, during the above stepwise process, after the formation of any branch layer (ie, the first branch layer, the second branch layer, etc.), an intermediate substitution that is different from the first chain extender A group (which may also be referred to as a “spacing chain extender”) (for example, but not limited to, a different multifunctional carboxylic acid or anhydride containing a reactive terminal functional group) It can react with the terminal hydroxyl groups of the formed branch layer. The terminal functional group of the intermediate substituent is then reacted with a second chain extender (which can be different from either the first chain extender or the spacing chain extender) to produce the desired structure and functionality. Can produce dendritic polymers having properties. One non-limiting example of such a method for forming a polyester-type dendritic polymer is described in US Pat. No. 6,569,956 at column 3, line 33 to column 4, line 42. (This disclosure is specifically incorporated by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein). Another non-limiting example of a method of forming a polyester-type dendritic polymer is described in US Pat. No. 5,663,247, column 7, line 52 to column 8, line 38, the disclosure of which The incorporated disclosure is specifically incorporated by reference to the extent that it does not conflict with the terms and definitions provided herein.

  Alternatively, the dendritic polymer can be formed by pre-forming a dendritic structure and then attaching the dendritic structure to a multivalent core. For example, a polyester-type dendritic polymer can be converted into a monofunctional, difunctional, trifunctional or polyfunctional carboxylic acid by condensing one or more hydroxy functional carboxylic acids at normal esterification temperatures. Dendritic by making it possible to form ester bonds with functional, bifunctional, trifunctional or polyfunctional alcohols or epoxides, or to produce ester bonds, ether bonds or other chemical bonds It can be formed by similar procedures that form the structure. The crude material used to generate the dendritic structure can be selected to provide each dendritic structure with a functional group at its active center. This active center functional group can be reacted with a multivalent core to bind the dendritic structure to the core and a plurality of terminal functional groups at the periphery of the dendritic structure. One non-limiting example of such a method for forming a polyester-type dendritic polymer is described in US Pat. No. 5,663,247 (“the '247 patent”), column 7, lines 23-51. Line, and in column 8, lines 1-38, this disclosure specifically to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein. Incorporated as a reference.

  As indicated above, polyester-type dendritic polymers can be made from ester units or polyester units, optionally combined with ether units or polyether units. For example, the dendritic polymer of the compatible coating can be a polyester-type dendritic polymer comprising a monomer core or polymer core having at least one reactive epoxide, hydroxyl, carboxyl or anhydride group. 1-100, and more generally 1-20 (eg, 2-8) branch layers may be added to the core. The branched layer is a monomeric or polymeric branch having at least three reactive groups, of which at least one is generally a hydroxyl group and at least one is a carboxyl group, an anhydride group or an epoxide group. It can be formed from a branch extender. As discussed above, the polyester-type dendritic polymer can also optionally include at least one spacing chain extender (which can be a compound having two reactive groups). . For example, the spacing chain extender may contain one hydroxyl group and one carboxyl or anhydride group, or an internal ester (eg, lactone) of such a compound. Further, as discussed above, the polyester-type dendritic polymer may also contain terminal functional groups (eg, hydroxyl groups, carboxyl groups or anhydride groups, and / or the dendritic polymer is Optionally, at least one monomeric or polymeric chain terminator may be fully or partially at the end of the chain and / or functionalized with different functional groups May be.

  As discussed above, the '301 patent describes some of the multivalent cores suitable for use in forming polyester-type dendritic polymers in column 2, line 45 to column 3, line 68. Some examples; in column 4, lines 1-55, some examples of chain extenders suitable for use in forming polyester-type dendritic polymers, and column 4, line 56 In column 5 to column 68, some examples of chain terminators suitable for use in forming polyester-type dendritic polymers are provided. Further non-limiting examples of multivalent cores that can be used in forming the polyester-type dendritic polymer are disclosed in the '247 patent, column 3, line 22 to column 4, line 45. Further non-limiting examples of chain extenders that can be used in forming the polyester-type dendritic polymer are disclosed in the '247 patent, column 4, line 45 to column 5, line 7. Further non-limiting examples of chain terminators that can be used in forming the polyester-type dendritic polymer are disclosed in the '247 patent, column 5, line 33 to column 6, line 60. Non-limiting examples of spacing chain extenders that can be used in forming the polyester-type dendritic polymer are disclosed in the '247 patent, column 5, lines 7-32. The foregoing portions of the disclosures of the '301 and' 247 patents are specifically incorporated by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein.

The dendritic polymer of the compatible coating may be a polyester-type dendritic polymer that is at least one of a dendritic branched polyester oligomer and a dendritic branched polyester acrylate oligomer. Non-limiting examples of commercially available polyester-type dendritic polymers that may be used, under the trademark BOLTORN ^(TM), H20 dendritic polymer containing terminal hydroxyl groups, H30 dendritic polymers, and H40 dendritic polymer gutter Mention may be made of polyester-type dendritic polymers which are from Perstorp Specialty Chemicals, Perstorp, Sweden. According to the manufacturer, these materials generally have a weight average molecular weight in the range of 1,000 amu to 4000 amu, with an average of 16, 32 and 64 H20, H30 and H40 materials, respectively. Having a terminal hydroxyl group. Another non-limiting example of a useful commercially available polyester-type dendritic polymer is a polyester acrylate oligomer commercially available from Sartomer Company of Exton, Pennsylvania, containing a terminal acrylate group referred to as CN2302. Another non-limiting examples of useful dendritic polymers, polyester - a blend of polyether dendritic polymers (e.g., Perstorp Specialty Chemicals, Perstorp, commercially available from Sweden, under the trademark BOLTORN ^(TM), and P500 It is said).

  Other non-limiting examples of dendritic polymers that can be used in the above compatible coatings include polyester-polyether blended dendritic polymers, epoxide-amine dendritic polymers, carbosilane-based dendritic polymers, amidoamine dendritic polymers. Polymer, polysulfide dendritic polymer, polysiloxane dendritic polymer, polyaminosulfide dendritic polymer, polyether dendritic polymer, polythioether dendritic polymer, polyester dendritic polymer, polyesteramide dendritic polymer, poly (ether ketone) dendritic polymer And so on. Further, as discussed above, such materials can be functionalized, for example, by reaction with an acrylating agent to provide terminal acrylic groups, or suitable chain terminators. Can be terminated using

  The further dendritic polymer of the compatible coating can be an amidoamine dendritic polymer, which can also be referred to as a polyamidoamine dense star polymer. See, for example, U.S. Pat. No. 4,558,120 ("'120 Patent"). The amidoamine dendritic polymer may be represented by the formula described in the '120 patent at column 7, lines 10-15. A description of amidoamine dendritic polymers and their preparation can be found in column 2, line 39 to column 9, line 18 of the '120 patent, the description of which is incorporated herein by reference. To the extent they do not conflict with the terms and definitions used, they are incorporated by reference.

  The dendritic polymer of the compatible coating can be an epoxide-amine dendritic polymer. Epoxide-amine dendritic polymers can be prepared by the following repetitive reaction sequence: (a) conversion of a moiety suitable for generation of primary amino groups; (b) primary amino groups generated in (a), and 1 A ring-opening addition reaction of an epoxide of a branched molecule having at least one epoxide moiety and having at least one moiety suitable for the generation of at least one primary amino group; and (c) the amino functionality of the dendritic polymer Termination reaction characterized by the addition reaction of at least one substituted or unsubstituted acrylate on (amino function). The end-forming reaction can be performed by using 2,3-epoxypropyl (meth) acrylate. Non-limiting examples of epoxide-amine dendritic polymers are described in US Pat. No. 5,760,142 (“the '142 patent”). The description of the '142 patent at column 1, line 65 to column 3, line 56 is incorporated by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein. The

  The dendritic polymer of the compatible coating can also be a carbosilane-based dendritic polymer. The carbosilane-based dendritic polymer comprises: (a) a central silane nucleus; (b) a plurality of dendrites comprising a carbosilane branching layer extending outwardly from the central silane nucleus, wherein the peripheral partial branch layer has a terminal silane group And (c) a carbosilane core having an arm of an additional polymer chain that exits from the core to the peripheral silane end. Non-limiting examples of carbosilane dendritic polymers are described in US Pat. No. 5,276,110, particularly in column 1, line 58 to column 5, line 5, which description is incorporated by reference. Is incorporated by reference to the extent that it does not conflict with the terms and definitions provided herein.

Further, the dendritic polymer of the compatible coating can be a dendritic polymer prepared by polycondensation of a cyclic anhydride with diisopropanolamine. Non-limiting examples of such dendritic polymers include DSM N. V. , Commercially available under the trademark HYBRANE ^™ and is prepared with acrylate and methacrylate ester functionalities. One specific non-limiting example of such a dendritic polymer is the commercially available HYBRANE ^™ H1500 dendritic polymer (unmodified).

  The dendritic polymer of the compatible coating can also be a polysiloxane dendritic polymer. Polysiloxane dendritic polymers can be prepared, for example and without limitation, by repeated silane hydroxylation and chloride substitution at silicon atoms. The preparation of certain polysiloxane dendritic polymers is described in Uchida et al. Am. Chem. Soc. 1990, 112, 7077-7079, the disclosure of which is specifically incorporated by reference to the extent that the incorporated disclosure does not conflict with the terms and definitions provided herein. See also US Pat. No. 6,889,735, column 5, line 60 to column 6, line 13 (this disclosure is incorporated by reference in the terms provided herein) To the extent that it does not contradict the definition, it is specifically incorporated as a reference).

  As discussed above, the terminal functional group of the last formed branch layer of the dendritic polymer can be functionalized (ie, reacted to form the dendritic polymer, if desired). Different terminal functional groups may be provided). For example, a polyester-type dendritic polymer containing terminal hydroxyl groups can be acrylated to provide acrylate functional groups at the periphery of the dendritic polymer. For example, but not limited herein, acrylation of the polyester-type dendritic polymer, and recovery and purification of the acrylated dendritic polymer are methods well known from the literature (for example, Kirk-Othmer Encyclopedia of Chemical Technology). (1980, Vol. 1, pp. 386-413) can be performed using the method described in the article “Acrylic Ester Polymers”. As will be appreciated by those skilled in the art, acrylation is generally a direct reaction (eg, esterification) of a molecule to be acrylated with, for example, acrylic acid, methacrylic acid, or crotonic acid (β-methacrylic acid), isocyanato Condensation with (meth) acrylates, or generally between 1: 0.1 and 1: 5, more usually between 1: 0.5 and 1: 1.5 Direct reaction with anhydrides and / or acyl halides corresponding to acrylic acid, methacrylic acid or crotonic acid in the molecular ratio of acid or crotonic acid, anhydride and / or acyl halide. Other non-limiting examples of acrylating agents include epoxide functional or anhydride functional acrylates and methacrylates (eg, glycidyl methacrylate). As will be appreciated by those skilled in the art, typically the acrylating agent is used in a stoichiometric molar excess.

  For example, the percentage of terminal functional groups on the dendritic polymer that can be functionalized by acrylation to provide terminal acrylate groups can vary. For example, according to various non-limiting embodiments disclosed herein, about 1-100% of the terminal functional groups of the dendritic polymer of the compatible coating can be functionalized. The percentage of terminal acrylate groups in the acrylated (ie functionalized) polyester-type dendritic polymer varies from 1 to 100%, such as from 20 to 100%, or from 40 to 100% (eg, from 45 to 100%). And can range between any combination of these percentages, including the percentages described.

  The dendritic polymer of the compatible coating can be a polyester-type dendritic polymer containing terminal hydroxyl groups (eg, those described above), or one or more of the terminal hydroxyl groups can be functionalized. The dendritic polymer can be provided having one or more different terminal functional groups. For example, as discussed above, the hydroxyl group of a polyester-type dendritic polymer can be functionalized to provide one or more terminal acrylate groups.

  The dendritic polymer of the compatible coating may include a terminal functional group that is at least one of hydroxyl, acrylate, acid, isocyanate, thiol, amine, epoxy, silane, and glycidyl. Furthermore, the dendritic polymers according to various non-limiting embodiments disclosed herein are independently at least two different which are hydroxyl, acrylate, acid, isocyanate, thiol, amine, epoxy, silane, or glycidyl. Functional groups can be included. Those skilled in the art will readily recognize methods for functionalizing dendritic polymers (eg, the polyester-type dendritic polymers discussed above) to incorporate one or more of the terminal functional groups discussed above. To do.

  The compatible coating comprising the dendritic polymer can be formed from a compatible coating composition comprising a dendritic polymer comprising a terminal functional group. Here, the terminal functional group is at least one of hydroxyl, acrylate, methacrylate, acid, isocyanate, thiol, amine, epoxy, silane, and glycidyl. Non-limiting examples of dendritic polymers containing terminal functional groups and methods for making the polymers are discussed above.

In addition to the dendritic polymers discussed above, compatible coating compositions from which the compatible coating can be obtained can further include:
(A) an epoxy-containing material containing at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is an epoxy group;
(B) an isocyanate-containing material containing at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is an isocyanate group;
(C) a (meth) acrylate-containing substance containing at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is a (meth) acrylate group Containing material; and / or (d) an aminoplast resin comprising at least two reactive functional groups.
Furthermore, the compatible coating composition from which the compatible coating can be obtained optionally comprises a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and at least one of an initiator and a catalyst. obtain.

  Non-limiting examples of epoxy-containing materials that can be used include epoxy containing at least one epoxy group and at least one of an acrylate group, an isocyanate group, a thiol group, a further epoxy group, a silane group, and a glycidyl group. Substances may be mentioned.

  The epoxy-containing material of the compatible coating composition can be an epoxy-containing material that includes at least two epoxy groups. Non-limiting examples of epoxy-containing materials containing at least two epoxy groups include the following formulas I, II, or mixtures thereof:

によって表され得、
ここで：
（ａ）Ｒ^１は、水素もしくはＣ_１−Ｃ_３アルキルのような基を表し得；
（ｂ）ｍは、２〜４の範囲に及ぶ整数を表し得；
（ｃ）Ａは、以下のような基：
（ｉ）Ｃ_２−Ｃ_２０アルキレン、置換されたＣ_２−Ｃ_２０アルキレン、Ｃ_３−Ｃ_２０シクロアルキレン、置換されたＣ_３−Ｃ_２０シクロアルキレン、置換されていないかもしくは置換されたアリーレン基（例えば、フェニレンもしくはナフチレン）、アリール（Ｃ_１−Ｃ_３）アルキレン、置換されたアリール（Ｃ_１−Ｃ_３）アルキレン（ここで上記アルキレン置換基およびシクロアルキレン置換基は、各々独立して、カルボキシ、ヒドロキシ、もしくはＣ_１−Ｃ_３アルコキシであり、そして上記アリーレン置換基およびアリール（Ｃ_１−Ｃ_３）アルキレン置換基は、各々独立して、カルボキシ、ヒドロキシ、Ｃ_１−Ｃ_３アルコキシ、もしくはＣ_１−Ｃ_３アルキルである）；
（ｉｉ）基−Ｃ（＝Ｏ）Ｒ^２（Ｏ＝）Ｃ−（ここでＲ^２は、Ｃ_２−Ｃ_２０アルキレンもしくはアリーレンのような基を表す）；
（ｉｉｉ）基−Ｒ^３−（ＯＲ^３−）_ｎもしくは−（ＯＲ^３）_ｎ−（ここでＲ^３は、Ｃ_２−Ｃ_４アルキレンのような基を表し、１〜２０の範囲に及ぶ整数を表す）、
（ｉｖ）フタロイル、イソフタロイル（ｉｓｏｐｈｔｈａｔｈｏｙｌ）、テレフタロイル、ヒドロキシル置換されたフタロイル、ヒドロキシル置換されたイソフタロイル、ヒドロキシル置換されたテレフタロイル；または
（ｖ）以下の式によって表される基：

And can be represented by
here:
(A) R ¹ may represent hydrogen or a group such as C ₁ -C ₃ alkyl;
(B) m may represent an integer ranging from 2 to 4;
(C) A is a group as follows:
_(I) C 2 _{-C 20} alkylene, substituted _C 2 _{-C 20 alkylene,} C 3 _{-C 20} cycloalkylene, substituted _C 3 _{-C 20} cycloalkylene, or substituted or unsubstituted arylene group (Eg, phenylene or naphthylene), aryl (C ₁ -C ₃ ) alkylene, substituted aryl (C ₁ -C ₃ ) alkylene (wherein the alkylene and cycloalkylene substituents are each independently carboxy , Hydroxy, or C ₁ -C ₃ alkoxy, and the arylene and aryl (C ₁ -C ₃ ) alkylene substituents are each independently carboxy, hydroxy, C ₁ -C ₃ alkoxy, or C ₁ -C is a ₃ alkyl);
(Ii) a group —C (═O) R ² (O═) C—, wherein R ² represents a group such as C ₂ -C ₂₀ alkylene or arylene;
(Iii) a group —R ³ — (OR ³ —) _n or — (OR ³ ) _n — (where R ³ represents a group such as C ₂ -C ₄ alkylene and is an integer ranging from 1 to 20) Represents)
(Iv) phthaloyl, isophthaloyl, terephthaloyl, hydroxyl-substituted phthaloyl, hydroxyl-substituted isophthaloyl, hydroxyl-substituted terephthaloyl; or (v) a group represented by the following formula:

（ここでＲ^４およびＲ^５は、各々独立して、Ｃ_１−Ｃ_４アルキル、塩素もしくは臭素のような基を表し、ｐおよびｑは、各々独立して、０〜４の範囲に及ぶ整数を表し、核：

(Wherein R ⁴ and R ⁵ each independently represents a group such as C ₁ -C ₄ alkyl, chlorine or bromine, and p and q are each independently an integer ranging from 0 to 4) Represents the nucleus:

は、独立して、二価のベンゼン基もしくは二価のシクロヘキサン基のような基を表し、そして

Independently represents a group such as a divalent benzene group or a divalent cyclohexane group, and

が二価のベンゼン基である場合、Ｇは、−Ｏ−、−Ｓ−、−Ｓ（Ｏ_２）−、−Ｃ（＝Ｏ）−、−ＣＨ_２−、−ＣＨ＝ＣＨ−、−Ｃ（ＣＨ_３）_２−、−Ｃ（ＣＨ_３）（Ｃ_６Ｈ_５）−、−（Ｃ_６Ｈ_４）−もしくは

Is a divalent benzene group, G is —O—, —S—, —S (O ₂ ) —, —C (═O) —, —CH ₂ —, —CH═CH—, —C. _{(CH 3) 2 -, -} C (CH 3) (C 6 H 5) -, - (C 6 H 4) - or

のような基を表すか；または

Represents a group such as

が二価のシクロヘキサン基である場合、Ｇは、−Ｏ−、−Ｓ−、−ＣＨ_２−もしくは−Ｃ（ＣＨ_３）_２−のような基を表す）；
を表し得、そして
（ｄ）Ｂは、Ｃ_２−Ｃ_２０アルキル、置換されたＣ_２−Ｃ_２０アルキル、Ｃ_３−Ｃ_２０シクロアルキル、置換されたＣ_３−Ｃ_２０シクロアルキル、上記置換されていないかもしくは置換されたアリール基（フェニルおよびナフチル）、アリール（Ｃ_１−Ｃ_３）アルキル、または置換されたアリール（Ｃ_１−Ｃ_３）アルキルのような基を表し、ここで上記アルキル置換基およびシクロアルキル置換基は、各々独立して、カルボキシ、ヒドロキシ、もしくはＣ_１−Ｃ_３アルコキシであり、上記アリールおよびアリール（Ｃ_１−Ｃ_３）アルキル置換基は、各々独立して、カルボキシ、ヒドロキシ、Ｃ_１−Ｃ_３アルコキシ、もしくはＣ_１−Ｃ_３アルキルである。

Is a divalent cyclohexane group, G represents a group such as —O—, —S—, —CH ₂ — or —C (CH ₃ ) ₂ —);
Can represent, and (d) B _is, C 2 _{-C 20} alkyl, substituted _C 2 _{-C 20 alkyl,} C 3 _{-C 20} cycloalkyl, substituted _C 3 _{-C 20} cycloalkyl, is said substituted Represents a group such as an unsubstituted or substituted aryl group (phenyl and naphthyl), aryl (C ₁ -C ₃ ) alkyl, or substituted aryl (C ₁ -C ₃ ) alkyl, wherein The group and the cycloalkyl substituent are each independently carboxy, hydroxy, or C ₁ -C ₃ alkoxy, and the aryl and aryl (C ₁ -C ₃ ) alkyl substituents are each independently carboxy, Hydroxy, C ₁ -C ₃ alkoxy, or C ₁ -C ₃ alkyl.

The epoxy-containing material of the compatible coating composition may also be represented by the following formulas I, II, or mixtures thereof, where R ¹ is hydrogen; A is:

（ここでＲ^４、Ｒ^５、ＥおよびＧは、上記で議論される様な基を表し得、そしてｐおよびｑは、上記で定義されるとおりである）；Ｃ_２−Ｃ_１０アルキレン；フェニレン；−Ｒ^３−（ＯＲ^３）_ｎ−もしくは−（ＯＲ^３）_ｎ−（ここでＲ^３およびｎは、本明細書中上記で定義されるものと同じであるかまたはフタロイルである）；そしてＢは、Ｃ_２−Ｃ_１０アルキル、フェニルもしくはフェニル（Ｃ_１−Ｃ_３）アルキルのような基を表す。

(Wherein R ⁴ , R ⁵ , E and G may represent groups as discussed above, and p and q are as defined above); C ₂ -C ₁₀ alkylene; phenylene —R ³ — (OR ³ ) _n — or — (OR ³ ) _n — (wherein R ³ and n are the same as defined herein above or are phthaloyl); B _represents a C 2 _{-C 10} alkyl, phenyl or phenyl _(C 1 -C ₃₎ groups such as alkyl.

  Specific non-limiting examples of epoxy-containing materials containing at least two epoxy groups that can be used in the compatible coating composition include glycerol polyglycidyl ether, diglycerol polyglycidyl ether, glycerol propoxylate triglycidyl ether, Trimethylolpropane triglycidyl ether, sorbitol polyglycidyl ether, poly (ethylene glycol) diglycidyl ether, poly (propylene glycol) diglycidyl ether, neopentyl glycol diglycidyl ether, N, N-diglycidyl-4-glycidyloxyaniline, N , N′-diglycidyl toluidine, 1,6-hexanediol diglycidyl ether, diglycidyl 1,2-cyclohexanedicarboxylate, Diglycidyl of glycidyl bisphenol A (eg, diglycidyl ether of bisphenol A), polymer of diglycidyl bisphenol A, poly (bisphenol A-co-epichlorohydrin) endcapped with glycidyl, hydrogenated bisphenol A propylene oxide adduct , Diglycidyl esters of terephthalic acid, diglycidyl 1,2,3,6-tetrahydrophthalate, spiroglycol diglycidyl ether, hydroquinone diglycidyl ether, and mixtures thereof.

  Non-limiting examples of isocyanate-containing materials that can be used in the compatible coating composition of the present invention include at least one isocyanate group and a hydroxyl group, acrylate group, acid group, further isocyanate group, thiol group, amine group, epoxy Mention may be made of isocyanate-containing materials comprising at least one of groups, silane groups, vinyl groups, allyl groups, and glycidyl groups. As used herein, the term isocyanate-containing material means at least one isocyanate group (which may be a blocked isocyanate group or an unblocked isocyanate group). Including substances containing.

  Non-limiting examples of isocyanate-containing materials that can be used that contain at least two reactive functional groups, at least one of which is an isocyanate group, may include: m-isopropenyl-α, α The product of the reaction of an acrylic functional monomer containing a vinyl ether group with isocyanic acid; an unsaturated monomer having a functional group selected from amino, hydroxy, thio and combinations thereof; and at least two functional isocyanates Product of reaction with an isocyanate-containing compound having a group; as well as any of the mixtures described above. Such isocyanate-containing materials and methods for preparing them are described in detail in US Pat. No. 6,025,026 at column 6, line 37 to column 8, line 65. That disclosure is specifically incorporated herein by reference.

  For example, the isocyanate-containing material can be selected from one or more polyisocyanates (eg, diisocyanates and triisocyanates, including biurets and isocyanurates). Any suitable diisocyanate biuret, including 1,4-tetramethylene diisocyanate and 1,6-hexamethylene diisocyanate, can be used as the isocyanate containing material in the preparation of the reaction products of the present disclosure. Bicyclic alicyclic diisocyanates such as isophorone diisocyanate and 4,4′-methylene-bis- (cyclohexyl isocyanate) can also be used. Examples of suitable aralkyl diisocyanates from which biurets can be prepared include meta-xylene diisocyanate and α, α, α ′, α′-tetramethyl meta-xylene diisocyanate, which itself can also be used as an isocyanate containing material in the preparation of the reaction product of the present disclosure.

  The trifunctional isocyanate is also an isocyanate-containing material (eg, isophorone diisocyanate trimer, triisocyanatononane, triphenylmethane triisocyanate, 1,3,5-benzene triisocyanate, 2,4,6-tolene isocyanate, As an adduct of trimethylol and tetramethylxylene diisocyanate sold by CYTEC Industries under the trade name CYTHANE 3160, and DESMODUR N 3300, which is commercially available from Bayer Corporation (which is the isocyanurate of hexamethylene diisocyanate) In addition, the isocyanate may be a cyclic isocyanate (eg hexamethylene diisocyanate and And isocyanurates of diisocyanates such as isophorane didiisocyanate).

  The polyisocyanate that can be used as an isocyanate-containing material is also one or more of the polyamines and / or polyols disclosed above that have been chain extended using appropriate materials and techniques known to those skilled in the art. Can be one of the following.

  The isocyanate-containing material of the compatible coating composition can be an isocyanate-containing material that includes at least two isocyanate groups. Non-limiting examples of isocyanate-containing materials containing at least two isocyanate groups include: toluene-2,4-diisocyanate; toluene-2,6-diisocyanate; diphenylmethane-4,4′-diisocyanate; 2,4′-diisocyanate; paraphenylene diisocyanate; biphenyl diisocyanate; 3,3′-dimethyl-4,4′-diphenylene diisocyanate; tetramethylene-1,4-diisocyanate; hexamethylene-1,6-diisocyanate; 2,4-trimethylhexane-1,6-diisocyanate; lysine methyl ester diisocyanate; bis (isocyanatoethyl) fumarate; isophorone diisocyanate (under the trademark DESMODUR PL 340) Commercially available from Bayer Materialscience, Pittsburgh, PA); ethylene diisocyanate; dodecane-1,12-diisocyanate; cyclobutane-1,3-diisocyanate; cyclohexane-1,3-diisocyanate; cyclohexane-1,4-diisocyanate; Hexahydrotoluene-2,4-diisocyanate; Hexahydrotoluene-2,6-diisocyanate; Hexahydrophenylene-1,3-diisocyanate; Hexahydrophenylene-1,4-diisocyanate; Perhydrodiphenylmethane-2,4 '-Diisocyanate; perhydrodiphenylmethane-4,4'-diisocyanate; naphthylene-1,5-diisocyanate; And mixtures thereof.

  As used herein, the terms “(meth) acryl”, “(meth) acrylic” or “(meth) acrylate” refer to the acrylic / acrylic / acrylate form and methacrylic / methacrylic of the indicated material. It is intended to cover both the / methacrylate forms. Non-limiting examples of (meth) acrylate-containing materials that can be used in the compatible coating composition can include the following: acrylate monomers and methacrylate monomers (multifunctional acrylates and multifunctional methacrylates (eg, bifunctional) , Trifunctional, tetrafunctional, and pentafunctional acrylates and methacrylates).

  The compatible coating can be prepared using acrylic or methacrylic monomers, or a mixture of acrylic and / or methacrylic monomers. The mixture of (meth) acrylic monomers may include monoacrylic functional monomers, diacrylic functional monomers, triacrylic functional monomers, tetraacrylic functional monomers, and pentaacrylic functional monomers.

Non-limiting examples of (meth) acrylate monomers include polyfunctional (meth) acrylates (eg, difunctional, trifunctional, tetrafunctional, and pentafunctional (meth) acrylates). Non-limiting examples of (meth) acrylates that can be used in compatible coating compositions according to the present invention include the following formula VI:
^{VI R 8 - (OC (=} O) C (R 9) = CH 2) s
And can be represented by
Wherein R ⁸ represents a group such as an aliphatic or aromatic group containing 2 to 20 carbon atoms, and optionally 1 to 20 alkyleneoxy bonds; R ⁹ is hydrogen, or Represents a group such as an alkyl group containing 1 to 4 carbon atoms, and s represents an integer ranging from 1 to 5. When s is greater than 1, R ⁸ is a linking group that joins together the acrylic functionality. Typically, R ⁹ is hydrogen or methyl and s is an integer ranging from 1 to 3. More specifically, di (meth) acrylate (when s is 2) can be represented by the following formula VII:

によって表され得、
ここでＲ^１０およびＲ^１２は、同じであっても異なっていてもよく、そして各々は、水素、もしくは１〜４個の炭素原子を含むアルキル基のような基、好ましくは、水素もしくはメチルを表し、そしてＲ^１１は、例えば、１〜２０個の炭素原子の炭化水素結合基（例えば、アルキレン基、１個以上のオキシアルキレン基（もしくは異なるオキシアルキレン基の混合物）；または以下の式ＶＩＩＩの基：

And can be represented by
Wherein R ¹⁰ and R ¹² may be the same or different and each is hydrogen or a group such as an alkyl group containing 1 to 4 carbon atoms, preferably hydrogen or methyl. R ¹¹ represents, for example, a hydrocarbon linking group of 1 to 20 carbon atoms (eg, an alkylene group, one or more oxyalkylene groups (or a mixture of different oxyalkylene groups); or Group:

を表し、ここで各Ｒ^１３は、独立して、水素もしくは１〜４個の炭素原子のアルキル基（例えば、メチル）のような基を表し；各Ｊは、独立してハロゲン原子（例えば、塩素）を表し；各ｔは、独立して０〜４の範囲に及ぶ整数（例えば、０〜１）を表し；そしてｕおよびｖは、０〜２０の範囲に及ぶ数（例えば、１〜１５、もしくは２〜１０）である。ｕおよびｖの値は、平均数であり、そして計算される場合、整数もしくは分数であり得る。

Wherein each R ¹³ independently represents a group such as hydrogen or an alkyl group of 1 to 4 carbon atoms (eg, methyl); each J independently represents a halogen atom (eg, Each t independently represents an integer ranging from 0 to 4 (eg 0 to 1); and u and v are numbers ranging from 0 to 20 (eg 1 to 15). Or 2 to 10). The values of u and v are average numbers and, when calculated, can be integers or fractions.

  The (meth) acrylate having an epoxy group has the following formula IX:

によって表され得、ここでＲ^１４およびＲ^１５は、同じであっても異なっていてもよく、そして各々独立して、水素もしくは１〜４個の炭素原子のアルキル基（例えば、メチル）のような基を表し；Ｒ^１６およびＲ^１７は、２〜３個の炭素原子を含むアルキレン基（例えば、エチレンおよびプロピレン）であり得、そしてｗおよびｘは、０〜２０の数（例えば、０もしくは１〜１５もしくは２〜１０）である。ｗおよびｘのうちの一方が０でありかつ他方が１である場合、残りの基Ｒ^１６もしくはＲ^１７は、以下の式Ｘ：

Where R ¹⁴ and R ¹⁵ may be the same or different and are each independently as hydrogen or an alkyl group of 1 to 4 carbon atoms (eg, methyl). R ¹⁶ and R ¹⁷ can be alkylene groups containing 2 to 3 carbon atoms (eg, ethylene and propylene) and w and x are numbers from 0 to 20 (eg, 0 or 1-15 or 2-10). When one of w and x is 0 and the other is 1, the remaining group R ¹⁶ or R ¹⁷ is represented by the following formula X:

を有する芳香族基（例えば、２，２−ジフェニレンプロパンラジカル（このフェニル基は、Ｃ_１〜Ｃ_４アルキル基もしくはハロゲン（例えば、メチルおよび／もしくは塩素）で置換され得る）から得られる基）であり得る。

Aromatic group having (e.g., 2,2-phenylene propane radical (the phenyl group, C ₁ -C ₄ alkyl or halogen (e.g., groups derived from may be substituted) with methyl and / or chlorine)) It can be.

  The compatible coating composition may further comprise an aminoplast resin. Aminoplast resins include condensation products of amines or amides with aldehydes and have at least two reactive groups. Suitable aminoplasts include substances having NH groups (eg, urea, melamine, benzoguanamine, glycouril and cyclic urea) and carbonyl compounds (eg, formaldehyde or higher aldehydes and ketones) and alcohols (eg, methanol). , Ethanol, butanol, propanol, and hexanol), the condensation products resulting from the reaction of alcohol and formaldehyde with melamine, urea, or benzoguanamine are the most common, but other Condensation products of amines and amides also include, for example, aldehyde condensation of triazines, diazines, triazoles, guanazines, guanamines, and alkyl-substituted and aryl-substituted melamines. Aminoplast resins are commercially available from Cytec Industries, Inc. under the trademarks CYMEL and RESIMENE, Non-limiting examples of such products include CYMEL® 345, 350 and And / or 370 resin, and RESIMENE® 717, 730, and / or 735 resin Suitable reactive functional groups on the aminoplast resin include reactive groups disclosed herein (eg, , Hydroxyl, acrylate, methacrylate, acid, isocyanate, thiol, amine, epoxy, silane, and glycidyl).

  As discussed above, the compatible coating composition that can be used to form a compatible coating according to the present invention optionally comprises a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof. May be included. As used herein, the phrase “at least partially hydrolyzed” of a phrase coupling agent refers to a coupling agent that is at least partially or fully hydrolyzed. Non-limiting examples of coupling agents that can be used can include silanes, titanates, and / or zirconates.

For example, the coupling agent can be a silane coupling agent represented by the following formula V:
_{^{V (R 18 O) y -Si-}} (R 19) z
Here for each being:
R ¹⁸ is independently unsubstituted or substituted with epoxy, glycidoxy, amino, vinyl, benzyl, styryl, (meth) acryloxy, mercapto, halogen, ureido, or alkoxy. Represents a group such as a hydrocarbon substituent having at most 20 carbon atoms;
R ¹⁹ is independently epoxy, glycidoxy, amino, vinyl, benzyl, styryl, (meth) acryloxy, mercapto, halogen, ureido, alkoxy, or aliphatic, cycloaliphatic, or unsubstituted, or Like aromatic hydrocarbon substituents with up to 20 carbon atoms, substituted with epoxy, glycidoxy, amino, vinyl, benzyl, styryl, (meth) acryloxy, mercapto, halogen, ureido, or alkoxy Or two R ¹⁹ groups joined together to form a C ₄ -C ₇ cycloalkyl or heterocyclic group (wherein the heteroatom is at least one of oxygen and nitrogen) Forming;
y represents an integer ranging from 1 to 4; and z represents an integer ranging from 0 to 3, with the sum of y + z being 4.

  If the compatible coating composition does not include a coupling agent, the dendritic polymer of the compatible coating composition may optionally include one or more terminal hydroxyl, (meth) acrylate, carboxylic acid, isocyano In addition to the thiol, amine, epoxy, or glycidyl group, it may contain at least one terminal silane group. Additionally or alternatively, at least one of the functional groups of the epoxy-containing material, the isocyanate-containing material, the (meth) acrylate-containing material, or the aminoplast resin material of the compatible coating composition is a silane group It can be.

  As indicated above, the compatible coating composition that can be used to form the compatible coating can optionally include at least one of an initiator and a catalyst. As used herein, the term “initiator” refers to a substance that initiates a chemical reaction. Further, as used herein, the term “catalyst” refers to a substance that increases the rate of a chemical reaction without itself undergoing any permanent chemical reaction.

  If the compatible coating composition includes at least one epoxy-containing material (as discussed above), the compatible coating composition generally produces an acid upon exposure to heat and / or actinic radiation. Thereby including at least one initiator (eg, thermal initiator and / or photoinitiator) that may facilitate curing of the epoxy-containing material. For example, and without limitation herein, the acid produced by the initiator may be a Lewis acid or a Bronsted acid. Furthermore, when the compatible coating composition comprises a silane coupling agent or at least a partial hydrolyzate thereof (as defined above), the acid produced by the initiator is also the pH of the composition. By reducing the ratio, condensation of the silane coupling agent can be facilitated. As used herein with reference to a coating, coating composition, or component thereof, the terms “cured”, “cured” and the like include curing, polymerization, crosslinking, cooling, and drying. It is intended to include processes that are not limited to these.

  Although not limited herein, in addition to at least one epoxy-containing material, the compatible coating composition may contain terminal (meth) acrylate groups (eg, acrylated polyester-type dendritic polymers (examples of which are referred to above). In addition to promoting curing (eg, cross-linking) of the dendritic polymer, the use of an initiator capable of generating both acid and free radicals It is expected that curing of the epoxy-containing material can be accelerated. A combination of an initiator capable of generating an acid and an initiator capable of generating a free radical may also be used.

  The initiator can be a photoinitiator that is adapted to produce an acid upon exposure to actinic radiation. Non-limiting examples of suitable photoinitiators that can be adapted to produce an acid upon exposure to actinic radiation include onium and iodosyl salts, aromatic diazonium salts, metal cesium salts, o-nitrobenzaldehyde, Sulfonate ester or aromatic alcohol, aromatic amide or imide N-sulfonyloxy derivative, aromatic oxime sulfonate, quinonediazide, benzoin in the chain Examples of the resin include a group.

  Specific non-limiting examples of onium salts that can be used with the various non-limiting embodiments disclosed herein include diaryliodonium salts and triarylsulfonium salts. Other suitable onium salts are described in US Pat. No. 5,639,802, column 8, line 59 to column 10, line 46, which description is incorporated by reference. Non-limiting examples of triarylsulfonium salts include triarylsulfonium hexafluorophosphate and triarylsulfonium hexafluoroantimonate. Non-limiting examples of diaryliodonium salts include 4,4′-dimethyldiphenyliodonium tetrafluoroborate, phenyl-4-octyloxyphenylphenyliodonium hexafluoroantimonate, dodecyldiphenyliodonium hexafluoroantimonate, [ 4-[(2-tetradecanol) oxy] phenyl] phenyliodonium hexafluoroantimonate, and mixtures of any of these.

  Further, when the compatible coating composition includes at least one isocyanate-containing material, the compatible coating composition generally includes a catalyst (which can be photocatalytic) that can promote curing of the isocyanate-containing material. . Non-limiting examples of suitable catalysts can include organotin catalysts and organobismuth catalysts. Further, in addition to the isocyanate-containing material, the compatible coating composition comprises an epoxy-containing material, a silane coupling agent or at least a partial hydrolyzate thereof, and / or a dendritic polymer containing terminal acrylate groups. The compatible coating composition is also adapted to produce an acid and may optionally further include an initiator that can produce free radicals to promote curing of these materials. Non-limiting examples of suitable initiators are described above.

  If the compatible coating composition includes a photoinitiator and / or photocatalyst, the photosensitive dye may optionally be capable of producing the chemical radiation required to activate the photoinitiator and / or photocatalyst. It can be added to the compatible coating composition to adjust the wavelength. Non-limiting examples of photosensitive dyes may include acridine cationic dyes, benzoflavin cationic dyes, benzophenone type basic dyes, perylene type dyes, fluorine type dyes, and mixtures and combinations of any of these.

  The compatible coating composition of the present invention may further comprise one or more additives that may protect the processing and / or performance of the composition or coating or articles obtained therefrom. Non-limiting examples of such additives include, for example, polymerization inhibitors, solvents, UV absorbers, but are not limited to light stabilizers, and hindered amine light stabilizers (HALS). A light stabilizer, a heat stabilizer, a mold release agent, a rheology control agent, a smoothing agent (including but not limited to a surfactant), a free radical scavenger, and any of these These combinations and mixtures may be mentioned.

The compatible coating comprising a dendritic polymer present on at least a portion of the surface of the substrate can be obtained from a compatible coating composition comprising:
(A) a dendritic polymer containing terminal functional groups;
(B) an epoxy-containing material containing at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is an epoxy group;
(C) an aminoplast resin containing at least two reactive functional groups;
(D) a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and, if necessary,
(E) Initiator.
For example, the dendritic polymer can be a dendritic polymer containing at least one terminal acrylate group; the epoxy-containing material can be an epoxy-containing material containing at least two epoxy groups; the aminoplast resin can be at least It can be an aminoplast resin containing two reactive functional groups; the coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof is a silane coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof. And the initiator can be a photoinitiator adapted to produce an acid upon exposure to actinic radiation. Dendritic polymers containing at least one terminal acrylate group, epoxy-containing materials containing at least two epoxy groups, aminoplast resins containing at least two reactive functional groups, silane coupling agents, and acids upon exposure to actinic radiation Suitable non-limiting examples of photoinitiators adapted to produce are described in detail above.

Further, the compatible coating comprising the dendritic polymer on at least a portion of the surface of the substrate can be obtained from a compatible coating composition comprising:
(A) a dendritic polymer containing terminal acrylate groups;
(B) an isocyanate-containing material comprising at least two isocyanate groups;
(C) an aminoplast resin containing at least two reactive functional groups;
(D) a silane coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and (e) optionally at least one of a catalyst and an initiator.

  For example, the dendritic polymer can be a dendritic polymer comprising at least one terminal acrylate group; the isocyanate-containing material can be at least two isocyanate groups (which can be blocked or unblocked). The aminoplast resin can be an aminoplast resin containing at least two reactive functional groups; the coupling agent, at least a partial hydrolyzate thereof, or The mixture can be a silane coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; the initiator can be a photoinitiator; the catalyst is an organotin catalyst and an organic bismuth catalyst. It can be at least one. A dendritic polymer comprising at least one terminal acrylate group, an isocyanate-containing material comprising at least two isocyanate groups (which may or may not be blocked), at least two reactive functionalities Suitable non-limiting examples of aminoplast resins containing groups, silane coupling agents, photoinitiators, and catalysts that can be used with these non-limiting embodiments are described above.

Further, the compatible coating comprising the dendritic polymer on at least a portion of the surface of the substrate can be obtained from a compatible coating composition:
(A) a dendritic polymer comprising a terminal (meth) acrylate;
(B) a (meth) acrylate-containing material comprising at least two (meth) acrylate groups;
(C) an aminoplast resin containing at least two reactive functional groups;
(D) a silane coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and, if necessary,
(E) An initiator that can be, for example, a photoinitiator.
Dendritic polymers containing terminal (meth) acrylate groups that can be used in connection with these non-limiting embodiments, (meth) acrylate containing materials containing at least two (meth) acrylate groups, amino containing at least two reactive functional groups Suitable non-limiting examples of plast resins; silane coupling agents, initiators, and more specifically photoinitiators are described in detail above.

  The compatible coating composition disclosed herein is based on total solids, for example, at least 20% by weight of a dendritic polymer (eg, 20-80% by weight of the compatible coating composition, based on total solids, 30 to 70% by weight of the compatible coating composition) based on total solids.

  The compatible coating composition may comprise from 5 to 50 wt% (eg, 10 to 40 wt% or 15 to 30 wt%) epoxy-containing material, isocyanate-containing material, (meth) acrylate-containing material, amino It may contain a plast resin, or a mixture of any of these.

  The compatible coating composition may comprise from 5 to 50 wt% (e.g., 10 to 40 wt%, or 15 to 30 wt%) of a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof based on total solids Can be included.

  The amount of initiator and / or catalyst present in the compatible coating composition disclosed herein can be any amount sufficient to provide the desired curing characteristics for the coating. The exact amount of initiator and / or catalyst used in the compatible coating composition disclosed herein can include several factors such as, but not limited to, curing conditions, desired curing time, etc. Depending on the type of initiator and / or catalyst required to achieve the desired curing characteristics. For example, the initiator and / or catalyst may be present in the compatible coating composition in an amount ranging from 0.1 to 10% by weight, based on total solids.

  The present invention also relates to compatible coatings obtained from compatible coating compositions that are essentially free of photochromic materials and that include isocyanate-containing materials and (meth) acrylate-containing materials. Such compatible coatings can include dendritic polymers or aminoplast resins, as desired. For example, the (meth) acrylate-containing material of the compatible coating composition can be a dendritic polymer (eg, the (meth) acrylate functionalized dendritic polymer described above), or the compatible coating composition can be Dendritic polymers containing functional groups other than (meth) acrylate groups may be included.

For example, the present invention provides an ophthalmic element that includes:
(A) an ophthalmic substrate;
(B) a compatible coating essentially free of photochromic material on at least a portion of the surface of the ophthalmic substrate, the compatible coating comprising:
(I) an isocyanate-containing material comprising at least two isocyanate groups;
(Ii) a (meth) acrylate-containing substance containing at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is a (meth) acrylate group Substance (iii) an aminoplast resin containing at least two reactive functional groups;
(Iv) a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof;
(V) at least one of an initiator and a catalyst;
A conformable coating formed from a conformable coating composition comprising: (c) an abrasion resistant coating in contact with at least a portion of the conformable coating at a position opposite the ophthalmic substrate. Non-functional organic coating.

  For example, according to these non-limiting embodiments, the isocyanate-containing material of the compatible coating composition includes at least two isocyanate groups, which may or may not be blocked. The (meth) acrylate-containing material can be a (meth) acrylate-containing material containing at least two (meth) acrylate groups; the aminoplast resin can have at least two reactive functional groups The coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof can be a silane coupling agent; the initiator can be a photoinitiator; and the catalyst Is at least one of an organotin catalyst or an organobismuth catalyst That. Specifics of these and other suitable isocyanate-containing materials, (meth) acrylate-containing materials, aminoplast resins, coupling agents, initiators, and catalysts that may be present in compatible coating compositions according to these non-limiting embodiments Non-limiting examples are described above.

  Although not limited herein, the compatible coating on at least a portion of the surface of the substrate also includes a functional organic coating that includes a liquid crystal material (ie, a liquid crystal coating) applied to the substrate. Can be an alignment coating. As used herein, the term “alignment coating” refers to a coating that includes at least a partially aligned alignment medium that can be used to provide proper placement or position relative to another substance or coating. Say. As used herein, the term “to order” (and other forms (eg, ordering, ordered, etc.)) is appropriate Providing placement or position (eg, alignment with another structure or material, or by some other force or effect). Thus, as used herein, “ordering” means a contact method for aligning a material, for example, by aligning the material with another structure or material, as well as, for example, Includes both non-contact methods to condition the material by exposing the material to external forces or effects (eg, polarized light, electric or magnetic fields, shear forces, etc.). Trimming can also include a combination of contact and non-contact methods. Further, as used herein, the term “aligning, to align” (and other forms (eg, aligning, aligned, etc.)) By means of interaction with another substance, compound or structure is meant to provide an appropriate arrangement or position. For example, but not limiting herein, a liquid crystal coating (ie, a coating that includes a liquid crystal material) can be at least partially aligned by contact with the surface of the alignment coating. As used herein, the term “liquid crystal material” refers to a liquid crystal mesogen or a material containing a liquid crystal mesogen (s), including but not limited to a monomer, oligomer, or polymer. .

  More specifically, since the liquid crystal material includes a mesogen having a cage or disk-like structure, a rigid longitudinal axis, and a strong dipole, the liquid crystal material is generally arranged to acquire an approximate direction or Can be aligned. Thus, the liquid crystal material may have approximately a mesogenic longitudinal axis of the material (or a portion of the material) approximately parallel to the common axis by external forces or interaction with another structure (eg, an alignment coating). Can be trimmed or aligned to obtain the direction of. As used herein, the term “general direction” refers to the predominant arrangement or orientation of a substance or structure. However, the substance or structure may have an approximate orientation even though it exists in some variation within the arrangement, provided that the substance or structure, or some portion thereof, is at least one dominant arrangement. It should be recognized that Non-limiting examples of liquid crystal materials that can be used to form the liquid crystal coatings disclosed herein are described in detail below.

  For example, if the compatible coating also serves as an alignment coating, at least a portion of the surface of the compatible coating can be rubbed using, for example, a textured cloth, a velvet brush, or the like, Alternatively, the surface can be textured in another way, for example by etching to impart the desired order to the surface of the compatible coating. Further, if the compatible coating also serves as an alignment coating, the compatible coating can be at least partially cured prior to rubbing or texturing the coating.

  The compatible coating and / or the compatible coating composition from which the compatible coating can be obtained may be essentially free of photochromic material. As used herein, with respect to the various coatings described herein, the term “essentially free of photochromic material” means that the coating contains less than a photochromic amount of such material. Or no photochromic material. As used herein, the term “photochromic” means having an absorption spectrum for at least visible light that varies in response to at least actinic radiation. As used herein, the term “photochromic material” is adapted to exhibit photochromic properties, ie, has an absorption spectrum for at least visible light that varies in response to at least actinic radiation. Means any substance that has been adapted. Further, as used herein, the term “photochromic amount” refers to the amount of photochromic material sufficient to impart a visually identifiable photochromic property to a coating or other article in which the photochromic material is incorporated. Means. Accordingly, the compatible coating composition from which the compatible coating is obtained that is essentially free of the compatible coating and / or the photochromic material may contain less than a photochromic amount of photochromic material, or no photochromic material. It may be that they are free of any photochromic material.

  As discussed above, the present invention also relates to an optical element, wherein the optical element includes a substrate (eg, including but not limited to the above), at least a portion of the surface of the substrate. A compatible coating comprising a dendritic polymer above and obtainable from the compatible coating composition (eg, those discussed above), as well as the compatible coating at a position opposite the substrate. Includes a functional organic coating other than an abrasion resistant coating in contact with at least a portion. As used herein, the term “functional organic coating” refers to an organic material (ie, on a weight percent basis) that imparts desirable properties or characteristics to the article to which the functional organic coating is connected. A coating mainly containing an organic compound or a hydrocarbon compound). The functional organic coating of the present invention can be obtained from a composition that includes primarily organic materials and may optionally include inorganic materials or other carbon compounds (eg, other additives). Other additives suitable for use in the functional organic coating include, for example, polymerization inhibitors, solvents, light stabilizers (eg, including but not limited to UV light absorbers and HALS). , Thermal stabilizers, mold release agents, rheology control agents, smoothing agents (including but not limited to surfactants), free radical scavengers, and any combinations and mixtures thereof. The functional organic coating may be at least one of a photochromic coating, an alignment coating, and a liquid crystal coating. Non-limiting examples of such functional organic coatings are described in more detail below.

  The functional organic coating in contact with at least a portion of the compatible coating can be a photochromic coating. As used herein, the term “photochromic coating” refers to a coating comprising a photochromic amount of at least one photochromic material. As discussed above, a photochromic coating can impart photochromic properties to an optical element (eg, an ophthalmic element) to which the photochromic coating is connected. Photochromic coatings generally have a first transparent state corresponding to the color of the photochromic material contained in the photochromic coating in their basic state form (ie, when not exposed to actinic radiation) and their activation. Having a second colored state corresponding to the color of the photochromic material included in the photochromic coating in a state form (ie, when exposed to actinic radiation). For example, if the optical element is an ophthalmic lens that includes the photochromic coating, the lens is colored from a transparent state when the wearer is exposed to UV light (eg, from sunlight). It can change to a state and can return to a transparent state when the wearer is not exposed to UV light.

  Non-limiting examples of photochromic coating compositions that can be used to prepare photochromic coatings according to various non-limiting embodiments disclosed herein are described below. Such photochromic coating compositions are known and can be made according to components and methods that are well understood and recognized by those skilled in the art. For example, a photochromic polyurethane coating composition that can be used to prepare a photochromic coating according to the present invention can be produced by a catalytic or non-catalytic reaction of an organic polyol component and an isocyanate component in the presence of a photochromic material. Materials and methods for the preparation of polyurethanes are described in Ullmann's Encyclopedia of Industrial Chemistry, Fifth Edition, 1992, Vol. A21, pages 665-716. Non-limiting examples of methods and materials (eg, organic polyols, isocyanates, and other components) that can be used to prepare the polyurethane coating are described in US Pat. No. 4,889,413, column 2, line 42. To column 12, line 21; and 6,187,444, column 2, line 52 to column 12, line 15. Other isocyanate-containing coating compositions (eg, mono-isocyanate coating compositions) disclosed in US Pat. No. 6,916,537 (“the '537 patent”), column 3, lines 1-12. A polyol containing at least one carbonate group (non-limiting examples of which are described in the '537 patent at column 7, line 38 to column 8, line 49), and at least one reactive isocyanate Group and at least one polymerizable double bond (non-limiting examples of which are described in the '537 patent, column 8, line 50 to column 9, line 44), and optionally A non-limiting example of an isocyanate (addition to a photochromic material), including additional copolymerizable monomers (non-limiting examples of which are described in the '537 patent at column 11, line 47 to column 20, line 43). Te) reaction product (non-limiting examples include to) according to the seventh fourth row, second line 37 column '537 patent. The disclosures referred to above are specifically incorporated herein by reference.

  Non-limiting examples of photochromic aminoplast resin coating compositions that can be used to produce a photochromic coating according to the present invention have at least two functional groups selected from hydroxyl, carbamate, urea, or any mixture thereof. Further components and aminoplast resins (eg, US Pat. No. 4,756,973, column 4, line 59 to column 7, line 3; US Pat. No. 6,506,488, column 2, line 43) Line to column 12 line 23; and U.S. Pat.No. 6,432,544 column 2 line 32 to column 14 line 5)). Can be prepared. The disclosures referred to above are specifically incorporated herein by reference.

  Non-limiting examples of photochromic polysilane coating compositions contemplated for use in preparing photochromic coatings include at least one silane monomer (eg, glycidoxypropyltrimethoxysilane, vinyltrimethoxysilane, methacryloxypropyltrimethoxy). Silane, tetramethoxysilane, tetraethoxysilane, and / or methyltrimethoxysilane) and the hydrolyzate as described above, US Pat. No. 4,556,605, column 4, lines 6-17. It can be prepared by combining at least one photochromic material as described in column 40, the disclosure of which is specifically incorporated herein by reference.

  Non-limiting examples of photochromic poly (meth) acrylate coating compositions contemplated for use in preparing the photochromic coatings of the present invention include photochromic materials and monofunctional, bifunctional or polyfunctional (meth). Acrylate (US Pat. No. 6,025,026, column 6, line 5 to column 11, line 28; US Pat. No. 6,150,430, column 2, line 51 to column 8) Line 58; and in US Pat. No. 6,602,603, column 2, line 60 to column 7, line 50). The disclosures referred to above are specifically incorporated herein by reference.

  Non-limiting examples of polyanhydride photochromic coating compositions that can be used to prepare photochromic coatings according to the present invention are disclosed in US Pat. No. 6,432,544, column 2, line 32 to column 14, column 5 It can be prepared by reaction of a hydroxyl functional component and a polymeric anhydride functional component in a composition comprising at least one organic photochromic material as described in the row. Non-limiting examples of hydroxyl functional components, anhydride functional components, and other components that can be used to prepare the polyanhydride photochromic coating are described in US Pat. No. 4,798,745. Column 2, line 67 to column 8, line 65; column 4,798,746, column 2, line 32 to column 11, line 45; and column 5,239,012 It is described in the third column, the 17th line to the sixth column, the 52nd line. Other suitable polyanhydride coating compositions are described in US Pat. No. 6,436,525 at column 2, line 15 to column 11, line 60. The disclosures referred to above are specifically incorporated herein by reference.

  Non-limiting examples of photochromic poly (meth) acrylamide coating compositions contemplated for use in preparing the photochromic coating include photochromic materials, N-alkoxymethyl (meth) acrylamide and at least one other co-polymer. A polymerizable ethylenically unsaturated composition comprising a polymerizable ethylenically unsaturated monomer (e.g., those described in US Pat. No. 6,060,001, column 2, line 6 to column 5, line 39). It can be prepared by combining the product with a free radical initiated reaction product. A method for preparing N-alkoxymethyl (meth) acrylamide functional polymers is described in US Pat. No. 5,618,586 at column 1, line 65 to column 7, line 2. The disclosures referred to above are specifically incorporated herein by reference.

  Non-limiting examples of photochromic epoxy resin coating compositions that can be used to prepare the photochromic coatings of the present invention include photochromic compounds, epoxy resins or polyepoxides, and column 3, column 50 of US Pat. No. 4,756,973. Line and column 7, line 3; and US Pat. No. 6,268,055, column 2, line 63 to column 17, line 3 obtain. The disclosures referred to above are specifically incorporated herein by reference.

  Other non-limiting examples of photochromic coating compositions that can be used to form the photochromic coatings disclosed herein include US Pat. No. 6,531,076, column 3, lines 4 through 4. The poly (urea-urethane) composition disclosed in column 10, line 49 may be mentioned, the disclosure of which is specifically incorporated herein by reference.

  Non-limiting examples of suitable photochromic materials include benzopyran, naphthopyran (eg, those disclosed in US Pat. No. 5,658,501, column 1, line 64 to column 13, line 36), Indeno-fused naphthopyrans (eg, those disclosed in US Pat. No. 5,645,767, column 1, line 10 to column 12, line 57); spiropyrans (eg, spiro (benzoindoline) naphthopyran, spiro) (Indoline) benzopyran, spiro (indoline) naphthopyran, spiro (indoline) quinopyran, and spiro (indoline) pyran); oxazines; ~ Disclosed in column 21 line 38); and metal dithiozonates (eg, US) Those disclosed in Patent No. 3,361,706) may be mentioned. The foregoing disclosure is specifically incorporated herein by reference.

  Additional non-limiting examples of photochromic compounds, polymerizable photochromic compounds, and complementary photochromic compounds that can be used are described in US Pat. No. 5,166,345, column 3, line 36 to column 14, line 3. No. 5,236,958, column 1, line 45 to column 6, line 65; 5,252,742, column 1, line 45 to column 6, line 65; No. 5,359,085, column 5, line 25 to column 19, 55; line 5,488,119, column 1, line 29 to column 7, line 65; No. 5,821,287, column 3, line 5 to column 11, line 39; 6,113,814, column 2, line 23 to column 23, line 28; Column 2, line 18 to column 8, line 60 of line 6,153,126; line 60, column 6, line 2,296,785; 47th line to 31st column, 5th line; 3rd column, No. 6,348,604; 26th line to 17th column, 15th line; and 1st column, No. 6,353,102 It is described in the 62nd line to the 11th column, the 64th line. The disclosures referred to above are specifically incorporated herein by reference.

  The functional organic coating that may be in contact with at least a portion of the compatible coating can be an alignment coating. As discussed above, the term “alignment coating” refers to a coating that includes at least a partially aligned alignment medium that can be used to impart an appropriate placement or position to another substance or coating. possible. Non-limiting examples of alignment coatings include friction-aligned alignment coatings, photo-aligned alignment coatings, and trimmed liquid crystal alignment coatings. As used herein, the terms “friction-aligned alignment coating” and “rubbed alignment coating” refer to friction or otherwise texturing at least a portion of the surface of the coating. , Refers to a coating that is at least partially trimmed. As used herein, the term “photo-aligned alignment coating” refers to a coating that is at least partially trimmed by exposure to polarized actinic radiation. A trimmed liquid crystal alignment coating can include a liquid crystal coating that is trimmed at least partially when exposed to an external force (eg, a magnetic field, electric field, electric field, or shear force). Although not limited herein, the alignment coating can impart desirable orientation characteristics to the optical elements to which they are connected.

  For example, the functional organic coating that is in contact with at least a portion of the compatible coating can be an alignment coating, and more specifically includes a polyimide that can be at least partially trimmed by friction. It can be an aligned coating that is oriented. The alignment coating can also be a photo-aligned alignment coating that includes a photo-alignment material that can be at least partially trimmed by exposure to polarized chemical radiation. As used herein, the term “photo-alignment material” means a material that can be at least partially trimmed by exposure to polarized chemical radiation. Non-limiting examples of photoalignment materials include cinnamate derivatives, azobenzene derivatives, coumarin derivatives, and ferulic acid derivatives. For example, the photoalignment material may be a cinnamate derivative (eg, polyvinyl cinnamate, polyvinyl ester of paramethoxycinnamic acid, or polyacrylic ester of paramethoxy cinnamic acid). Other non-limiting examples of suitable photoalignment materials and methods for forming photoaligned alignment coatings are disclosed in US Pat. No. 5,389,698, column 1, line 35 to column 4, 19 Line, the disclosure of which is incorporated herein by reference; and Kozenkov et al., “Photoanotropic Effects in Poly (Vinyl-Cinnamate) Derivatives and Thirr Applications”, Mol. Cryst. Liq. Cryst. , Vol. 409 (2004), pages 251-259 and 265, the disclosure of which is incorporated herein by reference. Further, the alignment coating can be an aligned liquid crystal alignment coating that includes a liquid crystal material that is at least partially aligned by exposure to an external force (eg, a magnetic field, electric field, or shear force).

  As discussed above, alignment coatings can be used, for example, to align liquid crystal coatings that are in contact. Thus, when the functional organic coating in contact with at least a portion of the compatible coating is an alignment coating, the optical element includes an at least partially aligned liquid crystal material connected to the optical element. A liquid crystal coating can further be included, and can be in direct contact with at least a portion of the alignment coating such that at least a portion of the liquid crystal material can be aligned with at least a portion of the alignment coating. As discussed above, as used herein, the term “liquid crystal coating” refers to a coating that includes a liquid crystal material; and the term “liquid crystal material” includes a liquid crystal mesogen or a liquid crystal mesogen. A substance (for example, but not limited to, a monomer, an oligomer, or a polymer). Non-limiting examples of liquid crystal materials that can be used to form the liquid crystal coating can include both lyotropic and thermotropic liquid crystal monomers, oligomers, and polymers. In further embodiments, the liquid crystal coating may include a thermotropic liquid crystal material.

  Specific non-limiting examples of liquid crystal monomers that can be used in connection with various non-limiting embodiments disclosed herein include monofunctional and polyfunctional liquid crystal monomers. Further, the liquid crystal monomer can be a crosslinkable liquid crystal monomer and can further be a photocrosslinkable liquid crystal monomer. As used herein, the term “photocrosslinkable” means a substance (eg, a monomer, oligomer, or polymer) that can be crosslinked upon exposure to actinic radiation. For example, photocrosslinkable liquid crystal monomers include liquid crystal monomers that are crosslinkable upon exposure to ultraviolet and / or visible light, with or without the use of polymerization initiators and / or catalysts. Non-limiting examples of crosslinkable liquid crystal monomers suitable for use in accordance with various non-limiting embodiments disclosed herein include acrylates, methacrylates, allyl groups, allyl ethers, alkynes, amino groups, anhydrides, And liquid crystal monomers having functional groups selected from epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, ureas, vinyl groups, vinyl ethers, and blends of any of these. Non-limiting examples of photocrosslinkable liquid crystal monomers suitable for use in at least partial coating of the alignment equipment of the present invention are selected from acrylates, methacrylates, alkynes, epoxides, thiols, and blends of any of these. And a liquid crystal monomer having a functional group.

  Liquid crystal oligomers and polymers suitable for use in the present invention can include both main chain liquid crystal oligomers and polymers, and side chain liquid crystal oligomers and polymers. Typically, although not limited in this specification, in main chain liquid crystal oligomers and polymers, cage-like or disk-like liquid crystal mesogens are mainly located in the skeleton of the oligomer or polymer. Further, although not limited in the present specification, in the side chain oligomer and polymer, the above-mentioned cage-like or disc-like liquid crystal mesogen is mainly located in the side chain of the oligomer or polymer. Furthermore, the liquid crystal oligomers and polymers can be crosslinkable and can be photocrosslinkable.

  Non-limiting examples of liquid crystal oligomers and polymers suitable for use in accordance with the present invention include acrylates, methacrylates, allyl groups, allyl ethers, alkynes, amino groups, anhydrides, epoxides, hydroxides, isocyanates, blocked isocyanates. , Siloxanes, thiocyanates, thiols, ureas, vinyl groups, vinyl ethers, and main and side chain oligomers and polymers having functional groups selected from any blend thereof. Non-limiting examples of photocrosslinkable liquid crystal oligomers and polymers suitable for use in accordance with various non-limiting embodiments disclosed herein include acrylates, methacrylates, alkynes, epoxides, thiols, and any of these Examples include oligomers and polymers having functional groups selected from blends. Further description of suitable non-limiting examples of liquid crystal monomers, oligomers and polymers (including photocrosslinkable monomers, oligomers and polymers) can be found in US Pat. No. 7,044,599 B2, column 8, line 4. To column 9, line 3, which disclosure is specifically incorporated herein by reference.

  Liquid crystal mesogens suitable for use in the present invention may include thermotropic liquid crystal mesogens and lyotropic liquid crystal mesogens. Non-limiting examples of suitable thermotropic liquid crystal mesogens may include colmatic (or bowl-shaped) liquid crystal mesogens, discotic (or discotic) liquid crystal mesogens, and cholesteric liquid crystal mesogens.

  Alternatively, as discussed above, the compatible coating itself can be an alignment coating that is friction oriented. Further, the functional organic coating in contact with the compatible coating can be another alignment coating (eg, an aligned liquid crystal alignment coating or a photoaligned alignment coating) or at least partially trimmed. A liquid crystal coating comprising a liquid crystal material that can be at least partially aligned with the applied compatible coating. Although not limited herein, the aligned liquid crystal coating may impart certain desirable optical properties (eg, variations in refractive index) to the optical element to which the aligned liquid crystal coating is connected. Further, as discussed in more detail below, the aligned liquid crystal coating may itself be used to provide, for example, but not limited to, polarizing coatings, polarizing coatings and photochromic coatings, and photochromic-dichroic coatings. Can be used to align materials or coatings. Non-limiting examples of liquid crystal materials that can be used in forming the aligned liquid crystal coating are discussed in detail above.

  The aligned liquid crystal coating can include a material adapted to exhibit dichroism, and at least a portion of the material adapted to exhibit dichroism is the at least partially aligned liquid crystal material. And at least partially aligned. As used herein, the term “material adapted to exhibit dichroism” refers to at least one of the components of transmitted light in which two orthogonal planes are more strongly polarized than the other. Means a substance that is adapted to absorb. Non-limiting examples of materials that are adapted to exhibit dichroism may include dichroic dyes and photochromic-dichroic dyes. As used herein, the term “dichroic dye” generally refers to a component of at least transmitted light that has a constant absorption spectrum and two orthogonal planes polarized more strongly than others. Means a dye that is adapted to absorb one of As used herein, the term “photochromic-dichroic dye” has an absorption spectrum for at least visible light that varies in response to at least actinic radiation, and two orthogonal planes are at least By a dye that absorbs at least one of the components of the transmitted light that is more strongly polarized in response to actinic radiation.

  Non-limiting examples of dichroic dyes may include those disclosed in US Pat. No. 7,044,599 at column 7, lines 18-56, the disclosure of which is hereby incorporated by reference. Incorporated specifically in the book as a reference.

  Non-limiting examples of photochromic-dichroic dyes that can be used are shown in US Patent Application Publication No. 2005/0004361, paragraphs 27 to 158, and 2005/0012998 A1, paragraphs 89 to 251. And the materials described therein, the disclosures of which are specifically incorporated herein by reference.

  Although not limited herein, the functional organic coating can be a polarizing coating comprising an aligned liquid crystal coating and an aligned dichroic dye. As used herein, the term “polarizing coating” refers to a coating that is adapted to limit the oscillation of the electromagnetic vector of wavelength to one direction or plane. In general, although not required, polarizing coatings comprising conventional dichroic dyes may have a constant (or “fixed”) brightness or color due to the presence of the dichroic dyes. For example, the polarizing coating may have a brownish or blueish color or brightness. Non-limiting examples of suitable polarizing coatings comprising aligned liquid crystal materials and dichroic dyes are described in US Patent Application Publication No. 2005/0151926, paragraphs 10 to 159, the disclosure of which is specifically incorporated herein. Is incorporated by reference.

  The polarizing coating may further include a photochromic material. When the photochromic material is present, the coating can be both a polarizing coating and a photochromic coating (ie, exhibiting both conventional polarizing properties and conventional photochromic properties). For example, the polarized and photochromic coating is primarily due to the lightness of the dichroic dye, the first colored polarization state when not exposed to chemical radiation, the lightness and photochromic of the dichroic dye. Due to the combined effect of the color of the substance, it may have a second colored polarization state when exposed to actinic radiation. For example, if the optical element is an ophthalmic lens that includes the polarized and photochromic coating, the lens is in a first colored polarization state when the wearer is not exposed to UV or chemical radiation from sunlight. To reversibly switch to a second colored polarization state when exposed to UV or chemical radiation from sunlight.

  Further, the functional organic coating can be a photochromic-dichroic coating comprising an aligned liquid crystal coating comprising aligned photochromic-dichroic dyes. As used herein, the term “photochromic-dichroic coating” refers to a coating that is adapted to exhibit both photochromic and polarization properties in response to at least actinic radiation. For example, according to various non-limiting embodiments disclosed herein, the functional organic coating is in response to at least actinic radiation from a first optically transparent unpolarized state to a second. It can be a photochromic-dichroic coating adapted to reversibly switch to a colored polarization state. For example, if the optical element is an ophthalmic lens that includes the photochromic-dichroic coating, the lens is optical when the wearer is not exposed to UV or chemical radiation (eg, from sunlight). It can reversibly switch from a highly transparent unpolarized state to a colored polarized state when the wearer is exposed to UV actinic radiation (eg, from sunlight). Non-limiting examples of such coatings are described in US Patent Application Publication No. 2005/0012998, paragraphs 11-442, the disclosure of which is specifically incorporated herein by reference.

  Other types of functional organic coatings that may be used in accordance with the present invention may include the following: paints (eg, colored used for decoration, protection, and / or identification of substrates) Liquids or pastes; and, for example, inks in making confirmation marks on security documents (eg, documents such as banknotes, passports, and driver's licenses that may be desired to be ratified or verified) A colored liquid or paste used to write and print on materials).

  Further, the optical element comprises at least one functional organic coating in contact with at least a portion of the compatible coating, and at least of the functional organic coating in contact with at least a portion of the compatible coating. One or more additional functional organic coatings connected to the portion may be included. For example, the functional organic coating in contact with at least a portion of the compatible coating can be an alignment coating, and the optical element is in contact with and aligned with at least a portion of the alignment coating; It may further include a liquid crystal coating comprising at least partially aligned liquid crystal material. Further, as discussed above, the aligned liquid crystal coating can include a material adapted to exhibit the dichroism, and at least a portion of the material adapted to exhibit the dichroism is , At least partially aligned with at least a portion of the at least partially aligned liquid crystal material.

  In addition to the compatible coating and the functional organic coating, at least one of a transition coating, a protective coating (eg, those discussed above), and an anti-reflective coating is at least a portion of the optical element. Can be connected to. As used herein, the term “transition coating” refers to a coating that assists in creating a gradient of properties between two coatings. For example, but not limited herein, a transition coating can help create a hardness gradient between a relatively hard coating and a relatively soft coating. Non-limiting examples of transition coatings (which may also be referred to as “tie-layers” or “bonded phase coatings”) include photocurable acrylate-based thin films (eg, US Pat. 2003/0165686, paragraphs 79 to 173; 2004/0207809, paragraphs 108 to 204; 2005/0196616, paragraphs 107 to 158; 2005/196617, paragraphs 24 to 129; 2005/196618, paragraphs 28 to 291; 2005/0196626, paragraphs 164 to 217; and 2005/196696, paragraphs 24 to 141). Are specifically incorporated herein by reference.

  As used herein, the term “antireflection coating” refers to a coating that increases the transmittance of light through the substrate by reducing the amount of light reflected by the substrate. Non-limiting examples of antireflective coatings include, for example, single layers or multiple layers of metal oxides, metal fluorides, or other such materials. Non-limiting examples of suitable antireflective coatings can be found in US Pat. No. 5,580,819 at column 2, line 50 to column 11, line 44, the disclosure of which is herein Specifically incorporated as a reference.

  For example, as shown in FIG. 1, the optical element can include a substrate 10 that includes an abrasion resistant coating 12 on at least a portion of the surface 11 of the substrate 10. Further, as shown in FIG. 1, a compatible coating 20 comprising a dendritic polymer as described herein may be present on at least a portion of the wear resistant coating 12 and is functional organic. A coating 30 (eg, a photochromic coating, alignment coating, or liquid crystal coating as described herein) may be present on at least a portion of the compatible coating 20. Further, as shown in FIG. 1, a transition coating 40 may be present on at least a portion of the functional organic coating 30, and a protective coating 50 may be present on at least a portion of the transition coating 40. obtain. Still further, although not shown in FIG. 1, an anti-reflective coating may be disposed on the protective coating 50 and / or on the surface of the substrate 10 at a location opposite the surface 11.

  Also, as shown in FIG. 2, the optical element may include a substrate 210 that includes an abrasion resistant coating 212 on at least a portion of its surface 211. Further, as shown in FIG. 2, a compatible coating 220 comprising a dendritic polymer, as described herein, may be present on at least a portion of the wear resistant coating 212 and A functional organic coating 230 (eg, a photo-aligned alignment coating) as described herein may be present on at least a portion of the compatible coating 220. Further, as shown in FIG. 2, a second functional organic coating 232 (eg, an aligned liquid crystal coating) as described herein is present on at least a portion of the functional organic coating 230. And a protective coating 250 as described herein may be present on at least a portion of the second functional organic coating 232.

  As shown in FIG. 3, the optical element also includes a substrate 310 that includes a conformal coating 320 comprising a dendritic polymer as described herein on at least a portion of its surface 311. obtain. A functional organic coating 330 (eg, photochromic coating, alignment coating, or liquid crystal coating) as described herein may be present on at least a portion of the compatible coating 320. Further, as shown in FIG. 3, a protective coating 350 may be present on at least a portion of the functional organic coating 330.

  As discussed above, the present invention further contemplates methods for making the optical elements described above. For example, the present invention relates to a method for making an optical element, the method comprising forming a compatible coating comprising a dendritic polymer on at least a portion of a surface of a substrate, and the compatible coating described above. Forming a functional organic coating other than an abrasion resistant coating on at least a portion of the substrate, so that the functional organic coating is compatible with the conformity at a position opposite to the surface of the substrate. Including a step in contact with at least a portion of the coating.

  Also provided is a method for forming an ophthalmic element, the method comprising the following steps: compatibility essentially free of photochromic material on at least a portion of the surface of the ophthalmic substrate Forming a coating, wherein the compatible coating is (i) an isocyanate-containing material comprising at least two isocyanate groups; (ii) a (meth) acrylate-containing material comprising at least two reactive functional groups. Wherein at least one of the at least two reactive functional groups is a (meth) acrylate group; (iii) an aminoplast resin containing at least two reactive functional groups; (Iv) a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and (v) an initiator and a catalyst A step obtained from a compatible coating composition comprising at least one of: at least a portion of the compatible coating by exposing at least a portion of the compatible coating to at least one of UV radiation and thermal radiation. Including at least partially curing; and forming a functional organic coating other than a hard coating on at least a portion of the compatible coating at a location opposite the ophthalmic substrate.

  As discussed above, the substrate on which the conformable coating is formed can include an abrasion resistant coating on at least a portion of its surface, the conformable coating comprising the abrasion resistant coating. In contact with at least a portion of Non-limiting examples of suitable substrates and abrasion resistant coatings are described above.

  Forming the compatible coating on at least a portion of the surface of the substrate includes, for example, spin coating, spray coating, spin and spray coating, roll on at least a portion of the substrate. Applying the compatible coating composition by one or more of coating, curtain coating, and dip coating (immersion coating) may be included. Alternatively, the step of forming the compatible coating on at least a portion of the surface of the substrate may include in-mold casting or overmolding.

  For example, if the compatible coating is formed by overmolding, the compatible coating composition can be applied to a mold, after which the compatible coating composition is spread between the mold and the surface of the substrate. Thus, the substrate can be placed in the mold to form a coating on at least a portion of the surface of the substrate. Alternatively, the substrate can be placed in the mold so that there is a gap between the mold and the surface of the substrate, after which the compatible coating composition is injected into the gap. To form a coating on at least a portion of the surface of the substrate.

  When the compatible coating is formed by in-mold casting, one or more layers of the compatible coating composition can be applied to the mold and at least partially cured, after which the substrate is coated with the coating. Can be cast on top. For example, according to one non-limiting embodiment, the optical resin used to form the substrate can be cast into the mold and over the compatible coating, after which the group It is at least partially cured to form the material.

  Prior to forming the compatible coating on at least a portion of the surface of the substrate, the surface may be cleaned and / or treated to provide a clean surface and the compatibility to the substrate. A surface can be provided that can enhance the adhesion of the coating. A commonly used effective cleaning and treatment is ultrasonic cleaning with an aqueous soap / surfactant solution; cleaning with an aqueous mixture of organic solvents (eg, a 50:50 mixture of isopropanol: water or ethanol: water). UV treatment; activated gas treatment (eg, treatment with low temperature plasma or corona discharge); and chemical treatment that results in hydroxylation of the substrate surface (eg, the surface is treated with an alkali metal hydroxide (sodium hydroxide)). Or an aqueous solution of potassium hydroxide) (this solution may also include a fluorosurfactant), but is not limited thereto. In general, the alkali metal hydroxide solution is a dilute aqueous solution (eg, 5-40 wt%, more typically 10-15 wt% (eg, 12 wt%) alkali metal hydroxide). For example, U.S. Pat. No. 3,971,872, column 3, lines 13-25; U.S. Pat. No. 4,904,525, column 6, lines 10-48; and United States See Patent No. 5,104,692, column 13, lines 10-59 (which describe the surface treatment of polymeric organic materials). These disclosures are specifically incorporated herein by reference.

  The surface treatment of the substrate may be a low temperature plasma treatment. Although not limited herein, the method allows for the treatment of a surface to enhance adhesion of a coating formed on the surface, and roughening the surface without affecting the rest of the article and / or Alternatively, it can be a clean and efficient way to change the physical surface by a chemically changing step. Inert gases (eg, argon) and reactive gases (eg, oxygen) have been used as plasma gases. An inert gas can roughen the surface, while a reactive gas (eg, oxygen) can roughen the surface exposed to the plasma by, for example, generating hydroxyl or carboxyl units on the surface, and Can be changed chemically. Oxygen can be used as a plasma gas. Although not limited herein, oxygen can provide a slight but efficient chemical modification of the surface and provide a slight but efficient physical roughening of the surface. Conceivable. As will be appreciated by those skilled in the art, the degree of roughening and / or chemical modification of the surface is a function of the plasma gas and plasma unit operating conditions (including length of processing time).

  The surface of the substrate subjected to plasma treatment can be at room temperature or can be slightly heated before or during the plasma treatment. Although not limited herein, according to various non-limiting embodiments, the temperature of the surface to be subjected to plasma treatment can be adversely affected by the plasma (roughening and slight chemistry). Can be maintained at a temperature below the temperature (other than the intended increase in surface area due to the mechanical modification step). One skilled in the art can readily select the plastic substrate to be treated to achieve improvements in the operating conditions of the plasma unit, as well as the adhesion of the overlaid film / coating on the plasma treated surface.

  After the step of forming the compatible coating and before the step of forming the functional organic coating, at least a portion of the compatible coating may be at least partially cured. For example, at least partially curing at least a portion of the compatible coating can include exposing the compatible coating to at least one of actinic radiation (eg, UV light and thermal radiation). Furthermore, curing of the compatible coating can be accomplished using a dual-cure process (ie, using a two-step process that includes a UV curing step and a thermal curing step). The curing step in the dual curing process can be performed continuously, i.e., immediately after one, the other so that the compatible coating is essentially fully cured before further processing, or Instead, the curing step is such that the compatible coating is partially cured using one curing step (either heat or UV) prior to the step of forming a further coating thereon. Can be done. The entire structure can then be subjected to the second curing step to complete curing of the compatible coating and the additional coating can be cured simultaneously. Such dual cure processes are well known in the art and are described in more detail below.

  The compatible coating composition comprises a dendritic polymer containing at least one terminal (meth) acrylate group; an epoxy-containing material containing at least two epoxy groups; a silane coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof And, when included with a photoinitiator adapted to generate acid upon exposure to actinic radiation, at least partially curing at least a portion of the compatible coating comprises: Alternatively, it may include a step of exposing to an electron beam beam (ie, ionizing radiation), and may further include a step of exposing the portion to thermal radiation.

  The compatible coating composition also comprises a dendritic polymer comprising at least one terminal acrylate group; an isocyanate-containing material comprising at least two isocyanate groups; a silane coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; A catalyst; and, if included, a photoinitiator, at least partially curing at least a portion of the compatible coating comprises exposing the portion to UV light, and then the portion to thermal radiation. An exposing step can be included.

  Further, if the compatible coating includes an isocyanate-containing material and a (meth) acrylate-containing material (discussed above), the compatible coating is applied prior to the step of forming the functional coating on the compatible coating. The functional coating can be at least partially cured using a dual curing process. Here, the coating is first exposed to UV or electron beam radiation and then to thermal radiation. As will be appreciated by those skilled in the art, UV curing typically requires the presence of at least one photoinitiator. Examples of photopolymerization processes and photoinitiators are described in US Pat. No. 6,602,603 at column 12, line 11 to line 37 and column 12, line 41 to column 13, line 36. The disclosure of which is incorporated herein by reference. Techniques that cure by electron beams typically do not require the presence of a photoinitiator. For example, the coating may be exposed to UV or electron beam radiation to at least partially cure the (meth) acrylate-containing material of the composition in one step and then to thermal radiation in another step. Exposure may cure at least partially the isocyanate-containing material of the composition. These curing steps can be performed, for example, continuously before the functional organic coating is formed thereon. Alternatively, one of the curing steps can be performed before the step of forming the functional organic coating on the compatible coating, and one of the curing steps is performed on the compatible coating. It can be performed after the step of forming the functional organic coating. For example, according to one non-limiting embodiment, the compatible coating can be exposed to UV light or electron beam radiation before forming the functional organic coating thereon, after which both coatings are Can be exposed to thermal radiation.

  The functional organic coating formed on at least a portion of the compatible coating can be at least one of a photochromic coating, an alignment coating, and a liquid crystal coating.

  If the functional organic coating can be a photochromic coating, the step of forming the photochromic coating comprises applying a coating composition comprising a photochromic amount of a photochromic material to at least a portion of the substrate, for example, spin coating, spraying. Applying by one or more of coating, spin and spray coating, roll coating, curtain coating, and dip coating may be included.

  Alternatively, the photochromic coating can be formed on the substrate by overmolding. For example, a coating composition comprising a photochromic amount of a photochromic material can be applied to a mold, after which the substrate is between the mold and at least a portion of the surface of the substrate. It can be placed in the mold so that it can be spread. Alternatively, the substrate can be placed in the mold such that a gap exists between the mold and the surface of the substrate, after which the photochromic coating composition is injected into the gap. The coating can be formed.

  Still further, a coating composition having a photochromic material of less than photochromic content or no photochromic material can be formed on the surface of the substrate, for example, by any of the methods described above, and then A photochromic material or an additional amount of photochromic material can be absorbed into the coating to form the photochromic coating.

  If the functional organic coating comprises an alignment coating, forming the alignment coating comprises applying a coating composition comprising alignment media to at least a portion of the compatible coating, at least a portion of the alignment media. At least partially trimming and at least partially curing at least a portion of the alignment media. Further, the step of at least partially preparing at least a portion of the alignment media can occur before, during or after the step of at least partially curing at least a portion of the alignment media.

  For example, the step of forming the alignment coating may include the step of applying a coating composition comprising a photoalignment material to at least a portion of the compatible coating, eg, a coating composition described herein. And applying at least a portion of the photoalignment material by exposing the photoalignment material to plane-polarized UV light and at least partially curing the photoalignment material. Can do. For example, according to this non-limiting embodiment, the photo-alignment material is a photo-alignable polymer network (or “PPN”) that forms the material (eg, column 2 of US Pat. No. 5,389,698). Lines 1 to 4, column 10; and Kozenkov et al., “Photoanotropic Effects in Poly (Vinyl-Cinamate) Derivatives and Their Applications,” Mol. Cryst. 251-267), the disclosures of which are hereby incorporated by reference.

  If the alignment coating includes an alignment coating that is photo-aligned, the step of forming the alignment coating applies a coating composition that includes a photo-alignment material, eg, a coating composition described herein. Applying at least a portion of the compatible coating by any of the methods, and at least partially conditioning the photoalignment material by exposing the photoalignment material to plane polarized UV light. And then, at least partially curing the trimmed portion of the photo-alignment material. For example, although not limited herein, according to this non-limiting embodiment, the photo-alignment material is an azobenzene derivative (eg, column 2, lines 28-94 of US Pat. No. 4,974,941). Column 9, line 63), the disclosure of which is hereby incorporated by reference.

  If the alignment coating comprises a friction-aligned alignment coating, the step of forming the alignment coating comprises applying a coating composition that includes a friction-aligned alignment material (eg, including but not limited to polyimide). Applying to at least a portion of the conformable coating, eg, by any of the methods for applying a coating composition described herein, at least a portion of the friction-aligned alignment material at least a portion. Curing, and then trimming at least a portion of the frictionally oriented alignment material by rubbing the portion with a suitable textured fabric.

  If the alignment coating comprises an aligned liquid crystal alignment coating, the step of forming the alignment coating comprises applying a coating composition comprising a liquid crystal material, eg, a coating composition described herein. Applying to at least a portion of the compatible coating by any of the methods; exposing at least a portion of the liquid crystal material to at least one of a magnetic field, an electric field, or a shear force; At least partially trimming; and at least partially curing at least a portion of the liquid crystal material. For example, the step of at least partially curing at least a portion of the liquid crystal material includes the step of exposing at least a portion of the liquid crystal material to UV radiation during or after the step of at least partially preparing the liquid crystal material. Can be included.

  Further, as discussed above, when the optical element includes an alignment coating, the optical element includes a liquid crystal material that includes a liquid crystal material that is at least partially aligned over at least a portion of the alignment coating. May further be included. In this example, the step of forming the liquid crystal coating includes, for example, at least a portion of the alignment coating by a liquid crystal material, for example, by any of the methods for applying a coating composition described herein. Applying above, and at least partially aligning at least a portion of the liquid crystal material and at least a portion of the alignment coating. For example, alignment of the liquid crystal material can be achieved by bringing the liquid crystal in contact with the alignment coating for either a room temperature or an elevated temperature for a time sufficient to achieve the desired level of alignment.

  Further, at least a portion of the liquid crystal material may be at least partially cured during or after alignment. For example, when the liquid crystal material includes a photocrosslinkable liquid crystal monomer, the step of at least partially curing at least a part of the liquid crystal material includes at least a part of the liquid crystal material. Exposure to UV light may be included during or after alignment.

  As discussed above, aligned liquid crystal coatings according to various non-limiting embodiments disclosed herein may further include materials adapted to exhibit dichroism. The material adapted to exhibit the dichroism may be blended with at least a portion of the liquid crystal material and / or at least a portion of the liquid crystal material prior to applying the liquid crystal material to the substrate. And can be at least partially aligned with at least a portion of the liquid crystal material to form a functional organic coating (eg, a polarizing coating or a photochromic-dichroic coating). Additionally or alternatively, a material adapted to exhibit the dichroism can be applied to the liquid crystal coating before or after alignment of the liquid crystal coating. For example, a substance adapted to exhibit the dichroism can be absorbed into at least a portion of the liquid crystal coating, either before or after aligning a portion of the liquid crystal coating, and the liquid crystal It may be at least partially aligned with at least a portion of the material to form a functional organic coating (eg, a polarizing coating or a photochromic-dichroic coating). Non-limiting examples of materials adapted to exhibit dichroism are discussed in detail above.

  Further, as discussed above, when the functional organic coating is an aligned liquid crystal coating that includes an aligned dichroic dye, the liquid crystal coating can be a polarizing coating, further adding conventional photochromic materials. (Ie, to form a polarized and photochromic coating). For example, the photochromic material can be blended with at least a portion of the liquid crystal material and / or bonded to at least a portion of the liquid crystal material before being applied to the portion of the substrate, and / or Photochromic material can be absorbed into the liquid crystal coating either before or after alignment with the alignment coating.

  Further, as discussed above, at least a portion of the compatible coating is at least for forming an alignment coating prior to forming the functional organic coating on at least a portion of the compatible coating. Can be partially trimmed. For example, at least a portion of the compatible coating is typically obtained by rubbing or etching portions of the compatible coating after the step of at least partially curing the portion of the compatible coating composition. It can be at least partially trimmed. The functional organic coating formed on at least a portion of the at least partially aligned compatible coating can be a liquid crystal coating that is at least partially aligned. The liquid crystal coating that is at least partially aligned can optionally include materials and / or photochromic materials adapted to exhibit at least one dichroism. Non-limiting methods for forming at least partially aligned liquid crystal coatings (which can include materials adapted to exhibit dichroic and / or photochromic materials) are described above. Yes.

  Furthermore, the liquid crystal coating can be adapted to the compatible coating without trimming at least a portion of the compatible coating. Optionally, according to these non-limiting embodiments, during or after the application of the liquid crystal coating, at least a portion of the liquid crystal coating is, for example, a magnetic field, electric field, or shear force. It can be at least partially trimmed by exposure to at least one of them. As discussed above, the liquid crystal coating thus arranged can be used as an alignment coating (eg, another liquid crystal coating) for another coating. Furthermore, the liquid crystal coating thus arranged can be used without further modification, for example, to impart certain desirable optical properties (eg, desired refractive index) to the optical element, or the trim can be trimmed. Liquid crystal coatings can be used to align materials adapted to exhibit dichroism. For example, as discussed above, a liquid crystal coating comprising an aligned liquid crystal material can be used to align a dichroic dye or photochromic-dichroic dye to produce a polarizing coating or photochromic-dichroic coating. Can be used.

  Further, although not required, one or more coatings (eg, transition coatings, protective coatings, and / or anti-reflective coatings) can also be formed on the optical element. For example, as described above with respect to FIG. 1, a transition coating can be formed on at least the functional organic coating, and a protective coating can be formed on at least a portion of the transition coating. Although not limited herein, when the functional organic coating is a photochromic coating and the protective coating is an abrasion resistant hard coat, the transition coating is a relatively soft photochromic coating and a relatively hard protective coating. Can provide a hardness gradient between the two.

  Various non-limiting embodiments of the invention or aspects thereof are specifically described by the following non-limiting examples. The following examples are intended merely as illustrative examples, modifications and variations thereof, and are within the spirit and scope of the invention as set forth in the claims, which are within the skill of the art. It should be recognized that this is obvious.

  In Part 1 of the Examples below, the materials and methods used to prepare coated lenses with or without a primer are described. In Part 2, the methods used for the adhesion test and the reported results are listed in Table 1.

(Part 1-Lens preparation)
Seven pairs of lens substrates, each measuring 74 mm in diameter and having the base curvatures listed in Table 1, were used. The test lens was treated with a corona discharge for 15 seconds from a Tantec Corona unit operating at 60 Hertz and 1.3 kVA units. The test lens was then cleaned with an automated process of rubbing the surface with soapy water, rinsed with deionized water and allowed to air dry. Composition A was spin coated onto one of each pair of lenses to give a wet film weight of about 0.025 g.

  Composition A was prepared by mixing in the following order, in amounts listed as weight percent, based on the total weight of the composition: Polyester acrylate oligomer obtained from Sartomer Corporation, Exton, Pennsylvania. Reported 45.9 wt% CN2302; 13.8 wt% EPON® 828 epoxy resin reported to be bisphenol A diglycidyl ether obtained from Miller-Stephenson, Danbury, Connecticut; 32.1 wt% SILQUEST reported to be γ-glycidoxypropyl-trimethoxysilane available from GE Silicones, Wilton, Connecticut -187 (R); and Sigma Aldrich, St. 8.3% by weight of triarylsulfonium hexafluorophosphate salt mixed in 50% by weight of propylene carbonate obtained from Louis, Missouri.

  The lens coated with Composition A above was placed from a lens to a lamp under a 6 "(15.24 cm) long ferrous iodide doped mercury bulb of type" D "400 Watts / inch. Placed 8 inches (30.32 cm) for 30 seconds until cured.

  These samples and uncoated lenses were then obtained from Rolli Technologies, Ltd. Coat with a solution of a photo-alignable polymer network, commercially available as ROLIC® ROP-108 / CP, available from Allschwiil, Switzerland. The CP name is reported to mean cyclopentanone. The coating solution was applied during a first spin rate of 612 RPM for 2 seconds. After coating application, the spin speed of each coated lens was increased to 1518 RPM over 12 seconds and then to 1933 RPM over 2 seconds. The coated lens is provided with the following temperatures by IR and / or convection oven (CO), as shown: 5 zones: zone 1-175 ° C. (IR); zone 2-175 ° C. (IR) Zone 3-155 ° C. (IR) and 150 ° C. (CO); zone 4-150 ° C. (CO), and zone 5-150 ° C. (CO) on a conveyor belt moving in 11 minutes on the infrared / Dry in convection oven; and cool to room temperature.

  After applying the photo-orientable polymer network to each of the test lenses, at least a portion of the photo-orientable polymer network is a fused silica polarizer having a transmission axis parallel to the long side of the rectangular filter. The filter was at least partially trimmed by exposure to linearly polarized UV light from the same type "D" bulb mentioned above for 35 seconds. The distance from the lamp to the lens was about 6 inches (15.24 cm). After preparing at least a portion of the photo-alignable polymer network, the lens was cooled to room temperature.

Composition B was applied to the lens by spin coating under conditions reaching a wet film weight of about 0.10 g. Composition B was prepared by mixing the materials in the following order: 39.9 mixed with 0.1 wt% BYK® UV3530 surfactant obtained from BYK Chemie, USA, Wallingford, Connecticut. Heated and maintained at 65 ° C .; added 4.4 wt% dichroic dye formulated to obtain gray; mixed for 60 minutes. Liquid crystal monomer was added (27.3 wt% RM 105 liquid crystal monomer reported as having molecular formula C ₂₃ H ₂₆ O ₆ available from EMD Chemicals, Inc., Gibbstown, New Jersey), and the composition was For 30 minutes. Next, EMD Chemicals, Inc. 27.2 wt% RM 257 liquid crystal monomer having molecular formula C ₃₃ H ₃₂ O ₁₀ available from, Gibbstown, New Jersey was added and the composition was mixed for 30 minutes. Next, 1.1 wt% bis- (2,6-dimethoxybenzoyl) phenylphosphine oxide was added and the composition was mixed for 30 minutes.

  The coated lens was placed on a conveyor belt using an infrared heating system having the following five temperature zones: 100 ° C .; 90 ° C .; 60 ° C .; 55 ° C .; The coated lens was moved through the five temperature zones in 5 minutes. The sample was then cooled to room temperature before entering the UV conveyor curing line.

The UV conveyor curing line had a nitrogen atmosphere with an oxygen level of less than 100 ppm. The conveyor was placed under one ultraviolet “type D” 157.5 J / sec / inch (400 watts / inch) ferrous iodide doped mercury lamp with a length of 10 inches. It was moved at 7.2 mm / second. The lamp power was set to 94% and the lamp was placed 20.3 cm (8.0 inches) above the conveyor. A converging funnel was placed under the lamp to direct the light flow to a 15.24 cm x 5.08 cm (6 inch x 2 inch) area for lens exposure. A 300 nm filter was placed under the funnel to block UV wavelengths longer than 300 nm for the lens. Each lens was exposed for 20 seconds under the UV lamp. The sample was then placed in a convection oven at 105 ° C. (221 ^° F.) for 3 hours and 15 minutes.

(Part 2-Adhesion test)
The adhesion of the coating formed from composition B on the test lens with or without composition A is known to those skilled in the art and is described herein below as a crosshatch tape peel adhesion test. (Tape Peel Adhesion test). For each example test lens, the “A” lens is without coating composition A and the “B” lens is with coating composition A. In a primary test or dry test, a cutting tool consisting of 11 X-acto® universal knife blades spaced approximately 1 mm apart (from tip to tip) and 0.65 mm thick was used. Then, a first length cut (eg, from the center of the lens to 3 mm from the edge of the 65 mm diameter lens) is made on the sample, followed by a second cut and a third cut. These cuts were made at 90 ° to and across the first cut. The second cut and third cut were separated from each other to provide separate cross hatch zones. A piece of Scotch® 250 tape (3M, St. Paul, Minnesota) 2.54 cm (1 inch) wide and 5 to 6.3 cm (2 to 2.5 inches) long was cut into the first cut. Applied in the direction and pressed to remove any bubbles. Prior to testing, the tape was stored at 23 ° C. ± 5 ° C. at a relative humidity of less than 60%. The tape was then peeled from the surface with a sharp, rapid, uniform and continuous movement. This procedure was repeated with a new piece of tape. A smaller piece of tape (1.5 cm) is placed in each of the cross hatch zones produced by the second and third cuts in a direction 90 ° to the direction of the first tape. Applied. The tape was peeled in the same manner as described above. The resulting lens was examined using a point light source and a loupe (looping / magnifying glass). The average of the percentage coating remaining from these two sites was determined and reported in Table 1 as the “primary” adhesion test results. The sample was placed in boiling water for 0.5 hours. The procedure was repeated after the sample was removed, dried and cooled to room temperature. The averaged results of this test are reported in Table 1 as “secondary” adhesion test results.

（１）ＰＰＧ Ｉｎｄｕｓｔｒｉｅｓ，Ｉｎｃ，Ｐｉｔｔｓｂｕｒｇｈ，Ｐｅｎｎｓｙｌｖａｎｉａによって市販されている、ＣＲ−６０７モノマー製造されたコーティングされていないレンズ
（２）ＰＰＧ Ｉｎｄｕｓｔｒｉｅｓ，Ｉｎｃ．，Ｐｉｔｔｓｂｕｒｇｈ，Ｐｅｎｎｓｙｌｖａｎｉａによって市販されているＴＲＩＶＥＸ（登録商標）モノマーから製造され、Ｙｏｕｎｇｅｒ Ｏｐｔｉｃｓ（Ｔｏｒｒａｎｃｅ，Ｃａｌｉｆｏｒｎｉａ）によって調製されたコーティングされていないレンズ
（３）ポリカーボネートモノマーから製造され、Ｙｏｕｎｇｅｒ Ｏｐｔｉｃｓ（Ｔｏｒｒａｎｃｅ，Ｃａｌｉｆｏｒｎｉａ）によって調製されたハードコートレンズ
（４）ポリカーボネートから製造されかつＰｏｌｙ ＧＬＣと指定されている、Ｇｅｎｔｅｘ Ｏｐｔｉｃｓ，Ｉｎｃ．，Ｄｕｄｌｅｙ，Ｍａｓｓａｃｈｕｓｅｔｔｓによって調製されたハードコートレンズ
（５）Ａｍｅｒｉｃａ，Ｄａｌｌａｓ，ＴｅｘａｓのＥｓｓｉｌｏｒによって調製されかつＭＲ８と指定されているコーティングされていないレンズ
（６）Ｓｅｉｋｏ Ｏｐｔｉｃａｌ Ｐｒｏｄｕｃｔｓ，Ｍａｈｗａｈ，Ｎｅｗ Ｊｅｒｓｅｙによって調製されかつ未コーティングＭＲ１０と指定されているレンズ
（７）Ｓｅｉｋｏ Ｏｐｔｉｃａｌ Ｐｒｏｄｕｃｔｓ，Ｍａｈｗａｈ，Ｎｅｗ Ｊｅｒｓｅｙによって調製されかつハードコートＭＲ１０と指定されているレンズ。

(1) Uncoated lens made of CR-607 monomer, marketed by PPG Industries, Inc, Pittsburgh, Pennsylvania (2) PPG Industries, Inc. , Manufactured from TRIVEX® monomer marketed by Pittsburgh, Pennsylvania, and prepared from uncoated lens (3) polycarbonate monomer prepared by Younger Optics (Torrance, California), Young Optics (Torrance, California) (4) Manufactured from polycarbonate and designated Poly GLC, Gentex Optics, Inc. (5) Uncoated lens prepared by Essilor of America, Dallas, Texas and designated MR8 (6) Prepared by Seiko Optical Products, Mahwah, New Jersey And a lens designated as uncoated MR10 (7) A lens prepared by Seiko Optical Products, Mahwah, New Jersey and designated as hard-coated MR10.

  As discussed above, the present invention has been described herein in connection with specific embodiments and examples, while the present invention contemplates the specific embodiments and examples disclosed above. It is intended to cover modifications that are within the spirit and scope of the invention, as defined but not limited by the appended claims. Further, it is to be understood that this description illustrates aspects of the invention in connection with a clear understanding of the invention. Accordingly, certain aspects of the invention that do not facilitate a better understanding of the invention have been shown in order to simplify the description, as will be apparent to those skilled in the art.

10, 210, 310: Substrate 11, 211, 311: Surface 12, 212: Abrasion resistant coating 20, 220, 320: Compatible coating 30, 230, 330: Functional organic coating 40: Transition coating 50, 250, 350: Protective coating

Claims (30)

Optical elements including:
(A) a substrate;
(B) a compatible coating comprising a dendritic polymer on at least a portion of the surface of the substrate; and (c) contacting at least a portion of the compatible coating at a position opposite the substrate. Functional organic coatings other than wear resistant coatings. The dendritic polymers include polyester-polyether blended dendritic polymers, dendritic branched polyester oligomers, dendritic branched polyester acrylate oligomers, epoxide-amine dendritic polymers, carbosilane-based dendritic polymers, amidoamine dendritic polymers. Polymers, polysulfide dendritic polymers, polysiloxane dendritic polymers, polyaminosulfide dendritic polymers, polyether dendritic polymers, polythioether dendritic polymers, polyester dendritic polymers, polyesteramide dendritic polymers, and poly (ether ketone) dendritic polymers The optical element according to claim 1, which is at least one of polymers. The compatible coating is formed from a compatible coating composition comprising a dendritic polymer containing terminal functional groups, wherein the terminal functional groups are hydroxyl, (meth) acrylate, acid, isocyano, thiol, amine, epoxy, silane, The optical element of claim 1, wherein the optical element is at least one of glycidyl and glycidyl. The optical element of claim 3, wherein the compatible coating composition further comprises at least one of the following:
(A) an epoxy-containing material comprising at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is an epoxy group;
(B) an isocyanate-containing material comprising at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is an isocyanate group;
(C) a (meth) acrylate-containing substance containing at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is a (meth) acrylate group Containing material; and (d) an aminoplast resin comprising at least two reactive functional groups. The compatible coating composition comprises a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; an initiator; a catalyst; a polymerization inhibitor; a solvent; a light stabilizer; a thermal stabilizer; The optical element of claim 4 further comprising at least one of a rheology control agent; a smoothing agent; and a free radical scavenger. The compatible coating composition is:
(A) a dendritic polymer containing terminal (meth) acrylate groups;
(B) an epoxy-containing material comprising at least two epoxy groups;
(C) an aminoplast resin containing at least two reactive functional groups;
(D) a silane coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and (e) a photoinitiator,
The optical element according to claim 4, comprising: The compatible coating composition is:
(A) a dendritic polymer containing terminal (meth) acrylate groups;
(B) an isocyanate-containing material comprising at least two isocyanate groups;
(C) an aminoplast resin containing at least two reactive functional groups;
(D) a silane coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof;
(E) a photoinitiator; and (f) an organotin catalyst,
The optical element according to claim 4, comprising: The optical element of claim 1, wherein the compatible coating is essentially free of photochromic material. The optical element is
(A) a substrate comprising an abrasion resistant coating in contact with at least a portion of the surface of the substrate;
(B) a compatible coating comprising a dendritic polymer in contact with at least a portion of the wear resistant coating;
(C) a functional organic coating in contact with at least a portion of the compatible coating, wherein the functional organic coating is at least one of an alignment coating, a photochromic coating, and a liquid crystal coating And (d) at least one of a transition coating, an abrasion resistant coating, and an antireflective coating on at least a portion of the functional organic coating;
The optical element of claim 1, comprising: A method for making an optical element comprising:
(A) forming a compatible coating comprising a dendritic polymer on at least a portion of the surface of the substrate; and (b) other than an abrasion resistant coating on at least a portion of the compatible coating. Forming a functional organic coating, such that the functional organic coating is in contact with at least a portion of the compatible coating at a location opposite the surface of the substrate;
Including the method. The method of claim 10, wherein the functional organic coating is at least one of an alignment coating, a photochromic coating, and a liquid crystal coating. Prior to the step of forming the functional organic coating on at least a portion of the compatible coating, at least a portion of the compatible coating is formed after at least partially curing the portion of the compatible coating. The method of claim 10, wherein the method is at least partially trimmed by rubbing or texturing at least a portion of the conformable coating. The functional organic coating is a liquid crystal coating comprising at least partially aligned liquid crystal material, and forming the functional organic coating comprises:
(A) applying a coating composition comprising a liquid crystal material on at least a portion of at least a portion of the conformable coating;
(B) at least partially aligning at least a portion of the liquid crystal material with at least a portion of at least a partially aligned portion of the compatible coating; and (c) at least a portion of the liquid crystal material. At least partially curing
The method of claim 12 comprising: (A) a dendritic polymer containing terminal functional groups;
(B) an epoxy-containing material containing at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is an epoxy group;
(C) an aminoplast resin containing at least two reactive functional groups;
(D) a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and (e) an initiator,
A compatible coating composition, wherein the compatible coating composition is essentially free of photochromic material. 15. The compatible coating composition of claim 14, wherein the dendritic polymer comprises at least 20% by weight of the compatible coating composition on a total solids basis. The dendritic polymers include dendritic branched polyester oligomers, dendritic polyester (meth) acrylate oligomers, epoxide-amine dendritic polymers, carbosilane-based dendritic polymers, amidoamine dendritic polymers, polysulfide dendritic polymers, polysulfides In at least one of siloxane dendritic polymer, polyaminosulfide dendritic polymer, polyether dendritic polymer, polythioether dendritic polymer, polyester dendritic polymer, polyesteramide dendritic polymer, and poly (ether ketone) dendritic polymer The compatible coating composition of claim 14. 15. The compatible coating of claim 14, wherein the terminal functional group of the dendritic polymer is at least one of hydroxyl, (meth) acrylate, acid, isocyanate, thiol, amine, epoxy, silane, and glycidyl. Composition. The compatible coating composition comprises an epoxy-containing material comprising an epoxy group and at least one of a (meth) acrylate group, an isocyanate group, a thiol group, an epoxy group, a silane group, and a glycidyl group. 15. A compatible coating composition according to 14. 15. The compatible coating composition of claim 14, wherein the epoxy-containing material comprises 5-50% by weight of the compatible coating composition on a total solids basis. 15. The compatible coating composition of claim 14, wherein the coupling agent comprises 5-50% by weight of the compatible coating composition on a total solids basis. The compatible coating composition of claim 14, wherein the initiator comprises at least one of a thermal initiator and a photoinitiator. (A) a substrate;
(B) a compatible coating obtained from the compatible coating composition of claim 14 on at least a portion of the surface of the substrate; and (c) on at least a portion of the compatible coating. A functional organic coating,
Including optical elements. A method for forming an ophthalmic element comprising:
Forming a compatible coating obtained from the compatible coating composition of claim 14 on at least a portion of the surface of the substrate; and (b) at least a portion of the compatible coating. On top, forming a functional organic coating;
Including the method. Prior to forming the functional coating on at least a portion of the compatible coating, at least a portion of the compatible coating at least partially cures a portion of the compatible coating composition. 24. The method of claim 23, wherein afterwards, at least partially trimmed by rubbing or texturing at least a portion of the conformable coating. (A) an ophthalmic substrate;
(B) a compatible coating essentially free of photochromic material on at least a portion of the surface of the ophthalmic substrate, the compatible coating comprising:
(I) an isocyanate-containing material comprising at least two isocyanate groups;
(Ii) a (meth) acrylate-containing substance containing at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is a (meth) acrylate group, Acrylate-containing materials;
(Iii) an aminoplast resin containing at least two reactive functional groups;
(Iv) a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and (v) at least one of an initiator and a catalyst;
A compatible coating formed from a compatible coating composition comprising: and (c) an abrasion resistant coating in contact with at least a portion of the compatible coating at a location opposite the ophthalmic substrate. Non-functional organic coating,
Including ophthalmic elements. The compatible coating composition is:
(A) an isocyanate-containing material comprising at least two isocyanate groups;
(B) a (meth) acrylate-containing material comprising at least two (meth) acrylate groups;
(C) an aminoplast resin containing at least two reactive functional groups;
(D) a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof;
(E) a photoinitiator; and (f) an organotin catalyst,
The ophthalmic element according to claim 25, comprising: 27. The ophthalmic element according to claim 26, wherein the (meth) acrylate containing material is a dendritic polymer. A method for forming an ophthalmic element comprising:
(A) forming a compatible coating essentially free of photochromic material on at least a portion of the surface of the ophthalmic substrate, wherein the compatible coating comprises:
(I) an isocyanate-containing material comprising at least two isocyanate groups;
(Ii) a (meth) acrylate-containing substance containing at least two reactive functional groups, wherein at least one of the at least two reactive functional groups is a (meth) acrylate group, Acrylate-containing materials;
(Iii) an aminoplast resin containing at least two reactive functional groups;
(Iv) a coupling agent, at least a partial hydrolyzate thereof, or a mixture thereof; and (v) at least one of an initiator and a catalyst;
Obtained from a compatible coating composition comprising:
(B) at least partially curing at least a portion of the compatible coating by exposing at least a portion of the compatible coating to at least one of UV radiation, electron beam radiation, and thermal radiation. And (c) forming a functional organic coating other than a hard coating on at least a portion of the compatible coating;
Including the method. Prior to forming the functional coating on at least a portion of the compatible coating, at least a portion of the compatible coating is at least partially rubbed by rubbing a portion of the compatible coating. 30. The method of claim 28, wherein the method is arranged. The functional organic coating is a liquid crystal coating that includes at least partially aligned liquid crystal material, and forming the functional organic coating on at least a portion of the compatible coating comprises:
(A) applying a coating composition comprising a liquid crystal material on at least a portion of the trimmed portion of the compatible coating; and (b) at least a portion of the liquid crystal material of the compatible coating. Aligning at least partially with the trimmed portion;
30. The method of claim 29, comprising:

Images